Adenine derivatives

ABSTRACT

This invention relates to an adenine derivative, a tautomer thereof, or a pharmaceutically acceptable salt thereof represented by general formula (I): 
                         
wherein X represents NR 3  (wherein R 3  represents a hydrogen atom or C 1-3  alkyl) or the like; R 1  represents substituted or unsubstituted alkyl or the like; R 2  represents hydroxyl or the like; and Y represents a substituted or unsubstituted aromatic hetero ring or the like. Also, the present invention relates to pharmaceuticals such as an interferon inducer, antiviral agent, anticancer agent, type 2 helper T cell selective immune response inhibitor, antiallergic agent, and immune response modulator comprising the above derivative as an active ingredient.

TECHNICAL FIELD

The present invention relates to an adenine derivative that is usefulfor preventing or treating viral diseases such as hepatitis B, hepatitisC, or AIDS, cancerous diseases, or the like. Also, the present inventionrelates to a pharmaceutical preparation such as an interferon inducer,antiviral agent, anticancer agent, type 2 helper T cell-selective immuneresponse inhibitor, antiallergic agent, or immune response modulatorcomprising the above derivative as an active ingredient.

BACKGROUND ART

Interferon is one of the most important factors that are in charge ofphylaxis or immune modulation. It has been already put to practical useas a therapeutic agent for hepatitis B and C and an immunotherapeuticagent for cancer. In particular, interferon is practically the onlytherapeutic agent available for hepatitis C. Interferon is a polypeptidehaving a molecular weight of about 20,000. It is produced by generecombination or cell culture, and it can be administered only in theform of injection. What is desired is, accordingly, the development ofan interferon inducer that can be orally administered.

Examples of known substances having interferon-inducing activity includedouble-stranded nucleic acids derived from viruses or other livingorganisms and high molecular weight polymers such as Poly(I)/Poly(C) orpolycarboxylate. Double-stranded nucleic acids or high molecular weightpolymers, however, are problematic in, for example, antigenicity,contamination by pathogenic microorganisms or biological stability. Inaddition, since they has a high molecular weight, development of oralpreparations therefrom is difficult. Several substances, such asfluorenones, pyrimidinones, or anthraquinones have been examined as lowmolecular weight interferon-inducing substances (Mayer, G. D., et al.:Science, 1970, 169, 1214, Nichol, F. R. et al.: Antimicrob. AgentsChemother., 1976, 9, 433, Stringfellow, D. A., et al.: Antimicrob.Agents Chemother., 1991, 15, 111). Because of their low therapeuticeffect or toxicity, however, development of pharmaceutical preparationstherefrom was relinquished (Reiter, M. A., et al.: J. Leukocyte Biol.1994, 55, 234). An imidazoquinoline derivative, R-837 (Imiquimod), isknown as another low molecular weight interferon-inducing substance (EP145,340). R-837, however, has low interferon-inducing activity, and thedevelopment thereof in the field of oral preparations was no longerperformed due to its side effects. The present inventors also found thata specific purine derivative had interferon-inducing activity (WO99-28321). Since these compounds had low water-solubility, they were notsufficient in terms of gastrointestinal absorption.

In contrast, helper T cells play major roles in immune responses. Thereare two types of helper T cells, i.e., Th1 cells and Th2 cells. Examplesof cytokines produced upon the activation of Th1 cells are interleukin-2(IL-2) and interferon-γ (IFN-γ). Examples of cytokines produced from Th2cells are interleukin-4 (IL-4) and interleukin-5 (IL-5). Th1 cytokinesactivate macrophages, natural killer cells, or the like, and they areknown to be mainly involved with cellular immunity such as phylaxisagainst viruses or bacteria. Th2 cytokines are involved with humoralimmunity such as antibody production from B cells. In particular, IL-4induces B cells to produce IgE antibodies and has actions of Th2 celldifferentiation or proliferation. IL-5 is capable of activatingeosinocytes, accelerating differentiation or proliferation, lifelengthening, or the like. Accordingly, it often plays a major role inallergic inflammation. In fact, these Th2 cytokines are increased inlesions of patients having allergic inflammation such as asthma oratopic dermatitis with which Th2 cells are mainly involved. Steroiddrugs are often used to treat these diseases. However, chronicadministration of steroid drugs disadvantageously generates a variety ofside effects such as diabetes, osteoporosis, adrenal disorder, or moonface. Since steroid drugs inhibitorily act against both T cells, i.e.,Th1 cells and Th2 cells, they may cause infectious diseases as a resultof inhibiting Th1 cells. Accordingly, pharmaceuticals that canselectively inhibit Th2 immune responses can be safe therapeutic agentsfor allergic diseases without causing infectious diseases.

DISCLOSURE OF THE INVENTION

An object of the present invention is to provide a low molecular weightcompound with improved physical properties (such as solubility orpharmacokinetics) that are effective for preventing or treating viraldiseases such as hepatitis B, hepatitis C, or AIDS, cancerous diseases,and diseases resulting from type 2 helper-T cells and that can be orallyadministered.

Under the above circumstances, the present inventors have conductedconcentrated studies. As a result, they found that an adenine derivativewith a specific structure had excellent interferon-inducing activity,type 2 helper T-cell-selective immune response inhibitory activity, andexcellent physical properties. This has led to the completion of thepresent invention.

More specifically, the present invention includes the following.

(1) An adenine derivative, a tautomer thereof, or a pharmaceuticallyacceptable salt thereof represented by general formula (I):

wherein X represents NR³ (wherein R³ represents a hydrogen atom or C₁₋₃alkyl), an oxygen atom, or a sulfur atom; R¹ represents substituted orunsubstituted alkyl, substituted or unsubstituted alkenyl, substitutedor unsubstituted alkynyl, substituted or unsubstituted aryl, orsubstituted or unsubstituted heteroaryl; R² represents hydroxyl,mercapto, C₁₋₈ acyloxy, or C₂₋₈ alkoxycarbonyloxy; and Y represents asubstituted or unsubstituted naphthalene ring, a substituted orunsubstituted 5- or 6-membered monocyclic aromatic hetero ringcontaining 1 or 2 hetero atoms selected from the group consisting ofnitrogen, oxygen, and sulfur atoms, or a substituted or unsubstitutedfused bicyclic aromatic hetero ring containing 1 or 2 hetero atomsselected from the group consisting of nitrogen, oxygen, and sulfuratoms.

(2) The compound according to (1) above, wherein, in general formula(I), R¹ represents C₁₋₈ alkyl, C₂₋₈ alkenyl, C₂₋₈ alkynyl, C₂₋₈alkoxyalkyl, C₁₋₈ hydroxyalkyl, aryl, heteroaryl, aralkyl, orheteroarylalkyl.

(3) The compound according to (1) or (2) above, wherein, in generalformula (I), R¹ represents C₁₋₆ alkyl.

(4) The compound according to any of (1) to (3) above, wherein, ingeneral formula (I), X represents NH.

(5) The compound according to any of (1) to (3) above, wherein, ingeneral formula (I), X represents an oxygen atom.

(6) The compound according to any of (1) to (5) above, wherein, ingeneral formula (I), Y represents a unsubstituted or substitutedpyridine ring or a substituted or unsubstituted pyrazine ring.

(7) The compound according to any of (1) to (5) above, wherein, ingeneral formula (I), Y represents a unsubstituted or substitutednaphthalene ring or a substituted or unsubstituted thiophene ring.

(8) The compound according to any of (1) to (6) above, wherein, ingeneral formula (I), Y has 1 to 4 substituents when Y is a pyridinering, and 1 to 3 substituents when Y is a pyrazine ring at anypositions, wherein the substituent is selected from the group consistingof C₁₋₄ alkyl, C₁₋₄ alkoxy, hydroxyl, mercapto, C₁₋₄ alkylthio, ahalogen atom, amino, C₂₋₈ dialkylamino, C₁₋₄ monoalkylamino,pyrrolidinyl, piperidino, and morpholino.

(9) The compound according to any of (1) to (6) and (8) above, wherein,in general formula (I), Y represents a pyridine ring which may have asubstituent selected from the group consisting of C₁₋₄ alkyl, C₁₋₄alkoxy, hydroxyl, mercapto, C₁₋₄ alkylthio, a halogen atom, amino, C₂₋₈dialkylamino, C₁₋₄ monoalkylamino, pyrrolidinyl, piperidino, andmorpholino; R¹ represents C₁₋₆ alkyl; and R² represents hydroxyl.

(10) The compound according to (9) above, wherein X represents NH or anoxygen atom.

(11) A pharmaceutical comprising, as an active ingredient, the compoundaccording to any of (1) to (10) above.

(12) An interferon inducer comprising, as an active ingredient, thecompound according to any of (1) to (10) above.

(13) An antiviral agent comprising, as an active ingredient, thecompound according to any of (1) to (10) above.

(14) An anticancer agent comprising, as an active ingredient, thecompound according to any of (1) to (10) above.

(15) A type 2 helper T cell selective immune response inhibitorcomprising, as an active ingredient, the compound according to any of(1) to (10) above.

(16) An antiallergic agent comprising, as an active ingredient, thecompound according to any of (1) to (10) above.

(17) An immune response modulator comprising, as an active ingredient,the compound according to any of (1) to (10) above.

The compounds according to the present invention are hereafter describedin detail.

In general formula (I), alkyl, alkenyl, or alkynyl represented by R¹ ispreferably C₁₋₈ alkyl, C₂₋₈ alkenyl, or C₂₋₈ alkynyl. Further, examplesof substituents of alkyl, alkenyl, or alkynyl represented by R¹ includehydroxyl, C₁₋₈ alkoxy, aryl, heteroaryl, and a halogen atom (e.g.,chlorine, fluorine, bromine, or iodine). Particularly preferableexamples of substituted alkyl, alkenyl, or alkynyl represented by R¹include C₂₋₈ alkoxyalkyl, C₁₋₈ hydroxyalkyl, aralkyl, andheteroarylalkyl.

Examples of the aforementioned C₁₋₈ alkyl include methyl, ethyl,1-propyl, 2-propyl, 1-butyl, 2-butyl, 1-pentyl, 2-pentyl, 1-hexyl,2-hexyl, 1-heptyl, 2-heptyl, 3-heptyl, octyl, 2-methylpropyl,2-methylbutyl, 3-methylbutyl, 2-methylpentyl, 3-methylpentyl,4-methylpentyl, methylhexyl, methylheptyl, 1,1-dimethylethyl,1,1-dimethylpropyl, 2-ethylhexyl, cyclopentylmethyl, cyclohexylmethyl,cyclopropyl, cyclobutyl, cyclopentyl, methylcyclopentyl, cyclohexyl,methylcyclohexyl, cycloheptyl, and cyclooctyl.

Examples of the aforementioned C₂₋₈ alkenyl include vinyl, allyl,crotyl, 1-propenyl, cyclopentenyl, cyclopentadienyl, and cyclohexenyl.

Examples of the aforementioned C₂₋₈ alkynyl include ethynyl, propynyl,and butynyl.

Examples of the aforementioned C₁₋₈ hydroxyalkyl include 1-hydroxyethyl,2-hydroxyethyl, 1-hydroxypropyl, 2-hydroxypropyl, 3-hydroxypropyl,1-hydroxybutyl, 2-hydroxybutyl, 3-hydroxybutyl, and 4-hydroxybutyl.

Examples of the aforementioned aralkyl include benzyl, 1-phenethyl,2-phenethyl, phenylpropyl, and phenylbutyl.

Examples of the aforementioned heteroarylalkyl include 4-pyridylmethyland 3-pyridylmethyl.

Examples of the aforementioned C₂₋₈ alkoxyalkyl include methoxymethyl,2-methoxyethyl, 3-methoxypropyl, 4-methoxybutyl, ethoxymethyl,2-ethoxyethyl, and 3-ethoxypropyl.

Each of the aforementioned substituents represented by R¹ may have asubstituent such as alkyl, hydroxyl, mercapto, a halogen atom, amino, oralkoxy.

In general formula (I), examples of aryl or heteroaryl represented by R¹include phenyl, 1-naphthyl, 2-naphthyl, 2-pyridyl, 3-pyridyl, 4-pyridyl,2-pyrazinyl, 3-pyrazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl,2-furyl, 3-furyl, 2-thienyl, and 3-thienyl. The aforementioned aryl orheteroaryl may or may not have a substituent. Examples of substituentsinclude C₁₋₄ alkyl, C₁₋₄ alkoxy, hydroxyl, mercapto, C₁₋₄ alkylthio, ahalogen atom, amino, C₂₋₈ dialkylamino, C₁₋₄ monoalkylamino, andmethylenedioxy. Examples of the aforementioned C₁₋₄ alkyl includemethyl, ethyl, 1-propyl, 2-propyl, 1-butyl, and 2-butyl. Examples ofC₁₋₄ alkoxy include methoxy, ethoxy, 1-propoxy, 2-propoxy, 1-butoxy, and2-butoxy. Examples of the aforementioned C₂₋₈ dialkylamino includedimethylamino, diethylamino, dipropylamino, dibutylamino,ethylmethylamino, and methylpropylamino. Examples of the aforementionedC₁₋₄ monoalkylamino include methylamino, ethylamino, propylamino, andbutylamino. Examples of the aforementioned C₁₋₄ alkylthio includemethylthio, ethylthio, 1-propylthio, 2-propylthio, 1-butylthio,2-butylthio, and t-butylthio. Examples of the aforementioned halogenatom include fluorine, chlorine, and bromine.

Examples of aryl or heteroaryl represented by R¹ having a substituentinclude 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2-ethylphenyl,3-ethylphenyl, 4-ethylphenyl, 2-propylphenyl, 3-propylphenyl,4-propylphenyl, 2-isopropylphenyl, 3-isopropylphenyl, 4-isopropylphenyl,2-butylphenyl, 3-butylphenyl, 4-butylphenyl, 2-chlorophenyl,3-chlorophenyl, 4-chlorophenyl, 2-fluorophenyl, 3-fluorophenyl,4-fluorophenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl,2-ethoxyphenyl, 3-ethoxyphenyl, 4-ethoxyphenyl, 2-propoxyphenyl,3-propoxyphenyl, 4-propoxyphenyl, 2-isopropoxyphenyl,3-isopropoxyphenyl, 4-isopropoxyphenyl, 2-butoxyphenyl, 3-butoxyphenyl,4-butoxyphenyl, 2-methylaminophenyl, 3-methylaminophenyl,4-methylaminophenyl, 2-ethylaminophenyl, 3-ethylaminophenyl,4-ethylaminophenyl, 2-propylaminophenyl, 3-propylaminophenyl,4-propylaminophenyl, 2-isopropylaminophenyl, 3-isopropylaminophenyl,4-isopropylaminophenyl, 2-butylaminophenyl, 3-butylaminophenyl,4-butylaminophenyl, 2-dimethylaminophenyl, 3-dimethylaminophenyl,4-dimethylaminophenyl, 2-diethylaminophenyl, 3-diethylaminophenyl,4-diethylaminophenyl, 2-dipropylaminophenyl, 3-dipropylaminophenyl,4-dipropylaminophenyl, 2-dibutylaminophenyl, 3-dibutylaminophenyl,4-dibutylaminophenyl, 2-ethylmethylaminophenyl,3-ethylmethylaminophenyl, 4-ethylmethylaminophenyl, 2-methylthiophenyl,3-methylthiophenyl, 4-methylthiophenyl, 2-ethylthiophenyl,3-ethylthiophenyl, 4-ethylthiophenyl, 2-propylthiophenyl,3-propylthiophenyl, 4-propylthiophenyl, 2-isopropylthiophenyl,3-isopropylthiophenyl, 4-isopropylthiophenyl, 2-butylthiophenyl,3-butylthiophenyl, 4-butylthiophenyl, 2-methyl-1-naphthyl,3-methyl-1-naphthyl, 4-methyl-1-naphthyl, 5-methyl-1-naphthyl,6-methyl-1-naphthyl, 7-methyl-1-naphthyl, 8-methyl-1-naphthyl,1-methyl-2-naphthyl, 3-methyl-2-naphthyl, 4-methyl-2-naphthyl,5-methyl-2-naphthyl, 6-methyl-2-naphthyl, 7-methyl-2-naphthyl,8-methyl-2-naphthyl, 2-methoxy-1-naphthyl, 3-methoxy-1-naphthyl,4-methoxy-1-naphthyl, 5-methoxy-1-naphthyl, 6-methoxy-1-naphthyl,7-methoxy-1-naphthyl, 8-methoxy-1-naphthyl, 1-methoxy-2-naphthyl,3-methoxy-2-naphthyl, 4-methoxy-2-naphthyl, 5-methoxy-2-naphthyl,6-methoxy-2-naphthyl, 7-methoxy-2-naphthyl, 8-methoxy-2-naphthyl,2-ethoxy-1-naphthyl, 3-ethoxy-1-naphthyl, 4-ethoxy-1-naphthyl,5-ethoxy-1-naphthyl, 6-ethoxy-1-naphthyl, 7-ethoxy-1-naphthyl,8-ethoxy-1-naphthyl, 1-ethoxy-2-naphthyl, 3-ethoxy-2-naphthyl,4-ethoxy-2-naphthyl, 5-ethoxy-2-naphthyl, 6-ethoxy-2-naphthyl,7-ethoxy-2-naphthyl, 8-ethoxy-2-naphthyl, 2-hydroxy-1-naphthyl,3-hydroxy-1-naphthyl, 4-hydroxy-1-naphthyl, 5-hydroxy-1-naphthyl,6-hydroxy-1-naphthyl, 7-hydroxy-1-naphthyl, 8-hydroxy-1-naphthyl,1-hydroxy-2-naphthyl, 3-hydroxy-2-naphthyl, 4-hydroxy-2-naphthyl,5-hydroxy-2-naphthyl, 6-hydroxy-2-naphthyl, 7-hydroxy-2-naphthyl,8-hydroxy-2-naphthyl, 2-chloro-1-naphthyl, 3-chloro-1-naphthyl,4-chloro-1-naphthyl, 5-chloro-1-naphthyl, 6-chloro-1-naphthyl,7-chloro-1-naphthyl, 8-chloro-1-naphthyl, 1-chloro-2-naphthyl,3-chloro-2-naphthyl, 4-chloro-2-naphthyl, 5-chloro-2-naphthyl,6-chloro-2-naphthyl, 7-chloro-2-naphthyl, 8-chloro-2-naphthyl,2-fluoro-1-naphthyl, 3-fluoro-1-naphthyl, 4-fluoro-1-naphthyl,5-fluoro-1-naphthyl, 6-fluoro-1-naphthyl, 7-fluoro-1-naphthyl,8-fluoro-1-naphthyl, 1-fluoro-2-naphthyl, 3-fluoro-2-naphthyl,4-fluoro-2-naphthyl, 5-fluoro-2-naphthyl, 6-fluoro-2-naphthyl,7-fluoro-2-naphthyl, 8-fluoro-2-naphthyl, 2-amino-1-naphthyl,3-amino-1-naphthyl, 4-amino-1-naphthyl, 5-amino-1-naphthyl,6-amino-1-naphthyl, 7-amino-1-naphthyl, 8-amino-1-naphthyl,1-amino-2-naphthyl, 3-amino-2-naphthyl, 4-amino-2-naphthyl,5-amino-2-naphthyl, 6-amino-2-naphthyl, 7-amino-2-naphthyl,8-amino-2-naphthyl, 2-methylamino-1-naphthyl, 3-methylamino-1-naphthyl,4-methylamino-1-naphthyl, 5-methylamino-1-naphthyl,6-methylamino-1-naphthyl, 7-methylamino-1-naphthyl,8-methylamino-1-naphthyl, 1-methylamino-2-naphthyl,3-methylamino-2-naphthyl, 4-methylamino-2-naphthyl,5-methylamino-2-naphthyl, 6-methylamino-2-naphthyl,7-methylamino-2-naphthyl, 8-methylamino-2-naphthyl,2-dimethylamino-1-naphthyl, 3-dimethylamino-1-naphthyl,4-dimethylamino-1-naphthyl, 5-dimethylamino-1-naphthyl,6-dimethylamino-1-naphthyl, 7-dimethylamino-1-naphthyl,8-dimethylamino-1-naphthyl, 1-dimethylamino-2-naphthyl,3-dimethylamino-2-naphthyl, 4-dimethylamino-2-naphthyl,5-dimethylamino-2-naphthyl, 6-dimethylamino-2-naphthyl,7-dimethylamino-2-naphthyl, 8-dimethylamino-2-naphthyl,2-methyl-3-pyridyl, 4-methyl-3-pyridyl, 5-methyl-3-pyridyl,6-methyl-3-pyridyl, 3-methyl-2-pyridyl, 4-methyl-2-pyridyl,5-methyl-2-pyridyl, 6-methyl-2-pyridyl, 2-methyl-4-pyridyl,3-methyl-4-pyridyl, 5-methyl-4-pyridyl, 6-methyl-4-pyridyl,2-ethyl-3-pyridyl, 4-ethyl-3-pyridyl, 5-ethyl-3-pyridyl,6-ethyl-3-pyridyl, 3-methyl-2-pyridyl, 4-methyl-2-pyridyl,5-methyl-2-pyridyl, 6-ethyl-2-pyridyl, 2-ethyl-4-pyridyl,3-ethyl-4-pyridyl, 5-ethyl-4-pyridyl, 6-ethyl-4-pyridyl,2-methoxy-3-pyridyl, 4-methoxy-3-pyridyl, 5-methoxy-3-pyridyl,6-methoxy-3-pyridyl, 3-methoxy-2-pyridyl, 4-methoxy-2-pyridyl,5-methoxy-2-pyridyl, 6-methoxy-2-pyridyl, 2-methoxy-4-pyridyl,3-methoxy-4-pyridyl, 5-methoxy-4-pyridyl, 6-methoxy-4-pyridyl,2-ethoxy-3-pyridyl, 4-ethoxy-3-pyridyl, 5-ethoxy-3-pyridyl,6-ethoxy-3-pyridyl, 3-ethoxy-2-pyridyl, 4-ethoxy-2-pyridyl,5-ethoxy-2-pyridyl, 6-ethoxy-2-pyridyl, 2-ethoxy-4-pyridyl,3-ethoxy-4-pyridyl, 5-ethoxy-4-pyridyl, 6-ethoxy-4-pyridyl,2-hydroxy-3-pyridyl, 4-hydroxy-3-pyridyl, 5-hydroxy-3-pyridyl,6-hydroxy-3-pyridyl, 3-hydroxy-2-pyridyl, 4-hydroxy-2-pyridyl,5-hydroxy-2-pyridyl, 6-hydroxy-2-pyridyl, 2-hydroxy-4-pyridyl,3-hydroxy-4-pyridyl, 5-hydroxy-4-pyridyl, 6-hydroxy-4-pyridyl,2-mercapto-3-pyridyl, 4-mercapto-3-pyridyl, 5-mercapto-3-pyridyl,6-mercapto-3-pyridyl, 3-mercapto-2-pyridyl, 4-mercapto-2-pyridyl,5-mercapto-2-pyridyl, 6-mercapto-2-pyridyl, 2-mercapto-4-pyridyl,3-mercapto-4-pyridyl, 5-mercapto-4-pyridyl, 6-mercapto-4-pyridyl,2-methylthio-3-pyridyl, 4-methylthio-3-pyridyl, 5-methylthio-3-pyridyl,6-methylthio-3-pyridyl, 3-methylthio-2-pyridyl, 4-methylthio-2-pyridyl,5-methylthio-2-pyridyl, 6-methylthio-2-pyridyl, 2-methylthio-4-pyridyl,3-methylthio-4-pyridyl, 5-methylthio-4-pyridyl, 6-methylthio-4-pyridyl,2-chloro-3-pyridyl, 4-chloro-3-pyridyl, 5-chloro-3-pyridyl,6-chloro-3-pyridyl, 3-chloro-2-pyridyl, 4-chloro-2-pyridyl,5-chloro-2-pyridyl, 6-chloro-2-pyridyl, 2-chloro-4-pyridyl,3-chloro-4-pyridyl, 5-chloro-4-pyridyl, 6-chloro-4-pyridyl,2-amino-3-pyridyl, 4-amino-3-pyridyl, 5-amino-3-pyridyl,6-amino-3-pyridyl, 3-amino-2-pyridyl, 4-amino-2-pyridyl,5-amino-2-pyridyl, 6-amino-2-pyridyl, 2-amino-4-pyridyl,3-amino-4-pyridyl, 5-amino-4-pyridyl, 6-amino-4-pyridyl,2-monomethylamino-3-pyridyl, 4-monomethylamino-3-pyridyl,5-monomethylamino-3-pyridyl, 6-monomethylamino-3-pyridyl,3-monomethylamino-2-pyridyl, 4-monomethylamino-2-pyridyl,5-monomethylamino-2-pyridyl, 6-monomethylamino-2-pyridyl,2-monomethylamino-4-pyridyl, 3-monomethylamino-4-pyridyl,5-monomethylamino-4-pyridyl, 6-monomethylamino-4-pyridyl,2-dimethylamino-3-pyridyl, 4-dimethylamino-3-pyridyl,5-dimethylamino-3-pyridyl, 6-dimethylamino-3-pyridyl,3-dimethylamino-2-pyridyl, 4-dimethylamino-2-pyridyl,5-dimethylamino-2-pyridyl, 6-dimethylamino-2-pyridyl,2-dimethylamino-4-pyridyl, 3-dimethylamino-4-pyridyl,5-dimethylamino-4-pyridyl, 6-dimethylamino-4-pyridyl,2-fluoro-3-pyridyl, 4-fluoro-3-pyridyl, 5-fluoro-3-pyridyl,6-fluoro-3-pyridyl, 3-fluoro-2-pyridyl, 4-fluoro-2-pyridyl,5-fluoro-2-pyridyl, 6-fluoro-2-pyridyl, 2-fluoro-4-pyridyl,3-fluoro-4-pyridyl, 5-fluoro-4-pyridyl, 6-fluoro-4-pyridyl,2,4-dimethyl-3-pyridyl, 2,6-dimethyl-3-pyridyl, 5,6-dimethyl-3-pyridyl,4,6-dimethyl-3-pyridyl, 4,5-dimethyl-2-pyridyl, 5,6-dimethyl-2-pyridyl,2,3-dimethyl-4-pyridyl, 2,6-dimethyl-4-pyridyl, 2,4-dimethoxy-3-pyridyl,2,6-dimethoxy-3-pyridyl, 5,6-dimethoxy-3-pyridyl,4,6-dimethoxy-3-pyridyl, 4,5-dimethoxy-2-pyridyl,5,6-dimethoxy-2-pyridyl, 2,3-dimethoxy-4-pyridyl,2,6-dimethoxy-4-pyridyl, 2-chloro-6-methyl-3-pyridyl,6-chloro-2-methyl-3-pyridyl, 2-chloro-6-methoxy-3-pyridyl,6-chloro-2-methoxy-3-pyridyl, 5-methyl-6-chloro-3-pyridyl,5-methoxy-6-chloro-3-pyridyl, 5-ethoxy-6-chloro-3-pyridyl,5-chloro-6-methyl-3-pyridyl, 5-methoxy-6-methyl-3-pyridyl,5-ethoxy-6-methyl-3-pyridyl, 5-chloro-6-methoxy-3-pyridyl,5-chloro-6-ethoxy-3-pyridyl, 2,5,6-trimethyl-3-pyridyl, 2-pyrazinyl,5-methyl-2-pyrazinyl, 6-methyl-2-pyrazinyl, 5-methoxy-2-pyrazinyl,6-methoxy-2-pyrazinyl, 5-ethoxy-2-pyrazinyl, 6-ethoxy-2-pyrazinyl,5-chloro-2-pyrazinyl, 6-chloro-2-pyrazinyl, 3-methyl-2-furyl,4-methyl-2-furyl, 5-methyl-2-furyl, 2-methyl-3-furyl, 4-methyl-3-furyl,5-methyl-3-furyl, 3-methoxy-2-furyl, 4-methoxy-2-furyl,5-methoxy-2-furyl, 2-methoxy-3-furyl, 4-methoxy-3-furyl,5-methoxy-3-furyl, 3-chloro-2-furyl, 4-chloro-2-furyl, 5-chloro-2-furyl,2-chloro-3-furyl, 4-chloro-3-furyl, 5-chloro-3-furyl, 3-fluoro -2-furyl,4-fluoro-2-furyl, 5-fluoro-2-furyl, 2-fluoro-3-furyl, 4-fluoro-3-furyl,5-fluoro-3-furyl, 3-methyl-2-thienyl, 4-methyl-2-thienyl,5-methyl-2-thienyl, 2-methyl-3-thienyl, 4-methyl-3-thienyl,5-methyl-3-thienyl, 3-methoxy-2-thienyl, 4-methoxy-2-thienyl,5-methoxy-2-thienyl, 2-methoxy-3-thienyl, 4-methoxy-3-thienyl,5-methoxy-3-thienyl, 3-chloro-2-thienyl, 4-chloro-2-thienyl,5-chloro-2-thienyl, 2-chloro-3-thienyl, 4-chloro-3-thienyl,5-chloro-3-thienyl, 3-fluoro-2-thienyl, 4-fluoro-2-thienyl,5-fluoro-2-thienyl, 2-fluoro-3-thienyl, 4-fluoro-3-thienyl, and5-fluoro-3-thienyl.

In general formula (I), examples of substituents represented by R²include hydroxyl, mercapto, C₁₋₈ acyloxy, and C₂₋₈ alkoxycarbonyloxy.

Examples of the aforementioned C₁₋₈ acyloxy include formyloxy,acetyloxy, propionyloxy, butanoyloxy, pentanoyloxy, hexanoyloxy,heptanoyloxy, octanoyloxy, and benzoyloxy.

Examples of the aforementioned C₂₋₈ alkoxycarbonyloxy includemethoxycarbonyloxy, ethoxycarbonyloxy, propoxycarbonyloxy,butoxycarbonyloxy, pentyloxycarbonyloxy, hexyloxycarbonyloxy,heptyloxycarbonyloxy, isopropyloxycarbonyloxy, isobutyloxycarbonyloxy,t-butyloxycarbonyloxy, isopentyloxycarbonyloxy, andbenzyloxycarbonyloxy.

In general formula (I), X represents any of NR³, an oxygen atom, or asulfur atom, wherein the aforementioned R³ represents a hydrogen atom orC₁₋₃ alkyl, and examples of the alkyl include methyl, ethyl, n-propyl,and isopropyl.

In general formula (I), examples of 5- or 6-membered monocyclic aromatichetero rings containing 1 or 2 hetero atoms selected from a nitrogenatom, an oxygen atom, or a sulfur atom represented by Y includethiophene ring, furan ring, pyrrole ring, thiazole ring, isoxazole ring,oxazole ring, pyrazole ring, imidazole ring, pyridine ring, pyrazinering, pyrimidine ring, and pyridazine ring. Examples of fused bicyclicaromatic hetero rings containing 1 or 2 hetero atoms selected from anitrogen atom, an oxygen atom, or a sulfur atom include benzothiophenering, benzofuran ring, indole ring, benzothiazole ring, benzoxazolering, benzoimidazole ring, quinoline ring, and isoquinoline ring. Theaforementioned Y may be unsubstituted or partially substituted by asubstituent. Examples of preferable Y include naphthalene ring,thiophene ring, pyridine ring, and pyrazine ring, and these rings may beunsubstituted or partially substituted by a substituent. For example,when Y is a pyridine ring, one to four substituents may substitute atany position on a pyridine ring. When Y is a pyrazine ring, one to threesubstituents may substitute at any position on a pyrazine ring. When Yis substituted with two or more substituents, they may be the same ordifferent.

Examples of the substituents for Y include C₁₋₄ alkyl, C₁₋₄ alkoxy,hydroxyl, mercapto, C₁₋₄ alkylthio, a halogen atom, amino, C₂₋₈dialkylamino, C₁₋₄ monoalkylamino, 1-pyrrolidinyl, 2-pyrrolidinyl,3-pyrrolidinyl, piperidino, morpholino, and 3-morpholinyl. Alkyl in theaforementioned C₁₋₄ alkyl and C₁₋₄ alkoxy, further in the aforementionedC₂₋₈ dialkylamino and C₁₋₄ monoalkylamino is the same as that in theaforementioned case of R¹. Examples of the aforementioned C₁₋₄ alkylthioinclude methylthio, ethylthio, 1-propylthio, 2-propylthio, 1-butylthio,2-butylthio, and t-butylthio. Examples of the aforementioned halogenatom include fluorine, chlorine, and bromine.

Examples of Y having a substituent include 2-methyl-1-naphthyl,3-methyl-1-naphthyl, 4-methyl-1-naphthyl, 5-methyl-1-naphthyl,6-methyl-1-naphthyl, 7-methyl-1-naphthyl, 8-methyl-1-naphthyl,1-methyl-2-naphthyl, 3-methyl-2-naphthyl, 4-methyl-2-naphthyl,5-methyl-2-naphthyl, 6-methyl-2-naphthyl, 7-methyl-2-naphthyl,8-methyl-2-naphthyl, 2-methoxy-1-naphthyl, 3-methoxy-1-naphthyl,4-methoxy-1-naphthyl, 5-methoxy-1-naphthyl, 6-methoxy-1-naphthyl,7-methoxy-1-naphthyl, 8-methoxy-1-naphthyl, 1-methoxy-2-naphthyl,3-methoxy-2-naphthyl, 4-methoxy-2-naphthyl, 5-methoxy-2-naphthyl,6-methoxy-2-naphthyl, 7-methoxy-2-naphthyl, 8-methoxy-2-naphthyl,2-ethoxy-1-naphthyl, 3-ethoxy-1-naphthyl, 4-ethoxy-1-naphthyl,5-ethoxy-1-naphthyl, 6-ethoxy-1-naphthyl, 7-ethoxy-1-naphthyl,8-ethoxy-1-naphthyl, 1-ethoxy-2-naphthyl, 3-ethoxy-2-naphthyl,4-ethoxy-2-naphthyl, 5-ethoxy-2-naphthyl, 6-ethoxy-2-naphthyl,7-ethoxy-2-naphthyl, 8-ethoxy-2-naphthyl, 2-hydroxy-1-naphthyl,3-hydroxy-1-naphthyl, 4-hydroxy-1-naphthyl; 5-hydroxy-1-naphthyl,6-hydroxy-1-naphthyl, 7-hydroxy-1-naphthyl, 8-hydroxy-1-naphthyl,1-hydroxy-2-naphthyl, 3-hydroxy-2-naphthyl, 4-hydroxy-2-naphthyl,5-hydroxy-2-naphthyl, 6-hydroxy-2-naphthyl, 7-hydroxy-2-naphthyl,8-hydroxy-2-naphthyl, 2-chloro-1-naphthyl, 3-chloro-1-naphthyl,4-chloro-1-naphthyl, 5-chloro-1-naphthyl, 6-chloro-1-naphthyl,7-chloro-1-naphthyl, 8-chloro-1-naphthyl, 1-chloro-2-naphthyl,3-chloro-2-naphthyl, 4-chloro-2-naphthyl, 5-chloro-2-naphthyl,6-chloro-2-naphthyl, 7-chloro-2-naphthyl, 8-chloro-2-naphthyl,2-fluoro-1-naphthyl, 3-fluoro-1-naphthyl, 4-fluoro-1-naphthyl,5-fluoro-1-naphthyl, 6-fluoro-1-naphthyl, 7-fluoro-1-naphthyl,8-fluoro-1-naphthyl, 1-fluoro-2-naphthyl, 3-fluoro-2-naphthyl,4-fluoro-2-naphthyl, 5-fluoro-2-naphthyl, 6-fluoro-2-naphthyl,7-fluoro-2-naphthyl, 8-fluoro-2-naphthyl, 2-amino-1-naphthyl,3-amino-1-naphthyl, 4-amino-1-naphthyl, 5-amino-1-naphthyl,6-amino-1-naphthyl, 7-amino-1-naphthyl, 8-amino-1-naphthyl,1-amino-2-naphthyl, 3-amino-2-naphthyl, 4-amino-2-naphthyl,5-amino-2-naphthyl, 6-amino-2-naphthyl, 7-amino-2-naphthyl,8-amino-2-naphthyl, 2-methylamino-1-naphthyl, 3-methylamino-1-naphthyl,4-methylamino-1-naphthyl, 5-methylamino-1-naphthyl,6-methylamino-1-naphthyl, 7-methylamino-1-naphthyl,8-methylamino-1-naphthyl, 1-methylamino-2-naphthyl,3-methylamino-2-naphthyl, 4-methylamino-2-naphthyl,5-methylamino-2-naphthyl, 6-methylamino-2-naphthyl,7-methylamino-2-naphthyl, 8-methylamino-2-naphthyl,2-dimethylamino-1-naphthyl, 3-dimethylamino-1-naphthyl,4-dimethylamino-1-naphthyl, 5-dimethylamino-1-naphthyl,6-dimethylamino-1-naphthyl, 7-dimethylamino-1-naphthyl,8-dimethylamino-1-naphthyl, 1-dimethylamino-2-naphthyl,3-dimethylamino-2-naphthyl, 4-dimethylamino-2-naphthyl,5-dimethylamino-2-naphthyl, 6-dimethylamino-2-naphthyl,7-dimethylamino-2-naphthyl, 8-dimethylamino-2-naphthyl,3-methyl-2-thienyl, 4-methyl-2-thienyl, 5-methyl-2-thienyl,2-methyl-3-thienyl, 4-methyl-3-thienyl, 5-methyl-3-thienyl,3-methoxy-2-thienyl, 4-methoxy-2-thienyl, 5-methoxy-2-thienyl,2-methoxy-3-thienyl, 4-methoxy-3-thienyl, 5-methoxy-3-thienyl,3-chloro-2-thienyl, 4-chloro-2-thienyl, 5-chloro-2-thienyl,2-chloro-3-thienyl, 4-chloro-3-thienyl, 5-chloro-3-thienyl,3-fluoro-2-thienyl, 4-fluoro-2-thienyl, 5-fluoro-2-thienyl,2-fluoro-3-thienyl, 4-fluoro-3-thienyl, 5-fluoro-3-thienyl,3-methyl-2-furyl, 4-methyl-2-furyl, 5-methyl-2-furyl, 2-methyl-3-furyl,4-methyl-3-furyl, 5-methyl-3-furyl, 3-methoxy-2-furyl,4-methoxy-2-furyl, 5-methoxy-2-furyl, 2-methoxy-3-furyl,4-methoxy-3-furyl, 5-methoxy-3-furyl, 3-chloro-2-furyl,4-chloro-2-furyl, 5-chloro-2-furyl, 2-chloro-3-furyl, 4-chloro-3-furyl,5-chloro-3-furyl, 3-fluoro-2-furyl, 4-fluoro-2-furyl, 5-fluoro-2-furyl,2-fluoro-3-furyl, 4-fluoro-3-furyl, 5-fluoro-3-furyl,3-methyl-2-pyrrolyl, 4-methyl-2-pyrrolyl, 5-methyl-2-pyrrolyl,2-methyl-3-pyrrolyl, 4-methyl-3-pyrrolyl, 5-methyl-3-pyrrolyl,3-methoxy-2-pyrrolyl, 4-methoxy-2-pyrrolyl, 5-methoxy-2-pyrrolyl,2-methoxy-3-pyrrolyl, 4-methoxy-3-pyrrolyl, 5-methoxy-3-pyrrolyl,3-chloro-2-pyrrolyl, 4-chloro-2-pyrrolyl, 5-chloro-2-pyrrolyl,2-chloro-3-pyrrolyl, 4-chloro-3-pyrrolyl, 5-chloro-3-pyrrolyl,3-fluoro-2-pyrrolyl, 4-fluoro-2-pyrrolyl, 5-fluoro-2-pyrrolyl,2-fluoro-3-pyrrolyl, 4-fluoro-3-pyrrolyl, 5-fluoro-3-pyrrolyl,1-methyl-2-imidazolyl, 4-methyl-2-imidazolyl, 1-methyl-4-imidazolyl,2-methyl-4-imidazolyl, 5-methyl-4-imidazolyl, 1-methyl-5-imidazolyl,4-methoxy-2-imidazolyl, 2-methoxy-4-imidazolyl, 5-methoxy-4-imidazolyl,4-chloro-2-imidazolyl, 2-chloro-4-imidazolyl, 5-chloro-4-imidazolyl,4-fluoro-2-imidazolyl, 2-fluoro-4-imidazolyl, 5-fluoro-4-imidazolyl,2-methyl-3-pyridyl, 4-methyl-3-pyridyl, 5-methyl-3-pyridyl,6-methyl-3-pyridyl, 3-methyl-2-pyridyl, 4-methyl-2-pyridyl,5-methyl-2-pyridyl, 6-methyl-2-pyridyl, 2-methyl-4-pyridyl,3-methyl-4-pyridyl, 5-methyl-4-pyridyl, 6-methyl-4-pyridyl,2-ethyl-3-pyridyl, 4-ethyl-3-pyridyl, 5-ethyl-3-pyridyl,6-ethyl-3-pyridyl, 3-methyl-2-pyridyl, 4-methyl-2-pyridyl,5-methyl-2-pyridyl, 6-ethyl-2-pyridyl, 2-ethyl-4-pyridyl,3-ethyl-4-pyridyl, 5-ethyl-4-pyridyl, 6-ethyl-4-pyridyl,2-methoxy-3-pyridyl, 4-methoxy-3-pyridyl, 5-methoxy-3-pyridyl,6-methoxy-3-pyridyl, 3-methoxy-2-pyridyl, 4-methoxy-2-pyridyl,5-methoxy-2-pyridyl, 6-methoxy-2-pyridyl, 2-methoxy-4-pyridyl,3-methoxy-4-pyridyl, 5-methoxy-4-pyridyl, 6-methoxy-4-pyridyl,2-ethoxy-3-pyridyl, 4-ethoxy-3-pyridyl, 5-ethoxy-3-pyridyl,6-ethoxy-3-pyridyl, 3-ethoxy-2-pyridyl, 4-ethoxy-2-pyridyl,5-ethoxy-2-pyridyl, 6-ethoxy-2-pyridyl, 2-ethoxy-4-pyridyl,3-ethoxy-4-pyridyl, 5-ethoxy-4-pyridyl, 6-ethoxy-4-pyridyl,2-hydroxy-3-pyridyl, 4-hydroxy-3-pyridyl, 5-hydroxy-3-pyridyl,6-hydroxy-3-pyridyl, 3-hydroxy-2-pyridyl, 4-hydroxy-2-pyridyl,5-hydroxy-2-pyridyl, 6-hydroxy-2-pyridyl, 2-hydroxy-4-pyridyl,3-hydroxy-4-pyridyl, 5-hydroxy-4-pyridyl, 6-hydroxy-4-pyridyl,2-mercapto-3-pyridyl, 4-mercapto-3-pyridyl, 5-mercapto-3-pyridyl,6-mercapto-3-pyridyl, 3-mercapto-2-pyridyl, 4-mercapto-2-pyridyl,5-mercapto-2-pyridyl, 6-mercapto-2-pyridyl, 2-mercapto-4-pyridyl,3-mercapto-4-pyridyl, 5-mercapto-4-pyridyl, 6-mercapto-4-pyridyl,2-methylthio-3-pyridyl, 4-methylthio-3-pyridyl, 5-methylthio-3-pyridyl,6-methylthio-3-pyridyl, 3-methylthio-2-pyridyl, 4-methylthio-2-pyridyl,5-methylthio-2-pyridyl, 6-methylthio-2-pyridyl, 2-methylthio-4-pyridyl,3-methylthio-4-pyridyl, 5-methylthio-4-pyridyl, 6-methylthio-4-pyridyl,2-chloro-3-pyridyl, 4-chloro-3-pyridyl, 5-chloro-3-pyridyl,6-chloro-3-pyridyl, 3-chloro-2-pyridyl, 4-chloro-2-pyridyl,5-chloro-2-pyridyl, 6-chloro-2-pyridyl, 2-chloro-4-pyridyl,3-chloro-4-pyridyl, 5-chloro-4-pyridyl, 6-chloro-4-pyridyl,2-amino-3-pyridyl, 4-amino-3-pyridyl, 5-amino-3-pyridyl,6-amino-3-pyridyl, 3-amino-2-pyridyl, 4-amino-2-pyridyl,5-amino-2-pyridyl, 6-amino-2-pyridyl, 2-amino-4-pyridyl,3-amino-4-pyridyl, 5-amino-4-pyridyl, 6-amino-4-pyridyl,2-monomethylamino-3-pyridyl, 4-monomethylamino-3-pyridyl,5-monomethylamino-3-pyridyl, 6-monomethylamino-3-pyridyl,3-monomethylamino-2-pyridyl, 4-monomethylamino-2-pyridyl,5-monomethylamino-2-pyridyl, 6-monomethylamino-2-pyridyl,2-monomethylamino-4-pyridyl, 3-monomethylamino-4-pyridyl,5-monomethylamino-4-pyridyl, 6-monomethylamino-4-pyridyl,2-dimethylamino-3-pyridyl, 4-dimethylamino-3-pyridyl,5-dimethylamino-3-pyridyl, 6-dimethylamino-3-pyridyl,3-dimethylamino-2-pyridyl, 4-dimethylamino-2-pyridyl,5-dimethylamino-2-pyridyl, 6-dimethylamino-2-pyridyl,2-dimethylamino-4-pyridyl, 3-dimethylamino-4-pyridyl,5-dimethylamino-4-pyridyl, 6-dimethylamino-4-pyridyl,2-(1-pyrrolidinyl)-3-pyridyl, 4-(1-pyrrolidinyl)-3-pyridyl,5-(1-pyrrolidinyl)-3-pyridyl, 6-(1-pyrrolidinyl)-3-pyridyl,3-(1-pyrrolidinyl)-2-pyridyl, 4-(1-pyrrolidinyl)-2-pyridyl,5-(1-pyrrolidinyl)-2-pyridyl, 6-(1-pyrrolidinyl)-2-pyridyl,2-(1-pyrrolidinyl)-4-pyridyl, 3-(1-pyrrolidinyl)-4-pyridyl,5-(1-pyrrolidinyl)-4-pyridyl, 6-(1-pyrrolidinyl)-4-pyridyl,2-piperidino-3-pyridyl, 4-piperidino-3-pyridyl, 5-piperidino-3-pyridyl,6-piperidino-3-pyridyl, 3-piperidino-2-pyridyl, 4-piperidino-2-pyridyl,5-piperidino-2-pyridyl, 6-piperidino-2-pyridyl, 2-piperidino-4-pyridyl,3-piperidino-4-pyridyl, 5-piperidino-4-pyridyl, 6-piperidino-4-pyridyl,2-morpholino-3-pyridyl, 4-morpholino-3-pyridyl, 5-morpholino-3-pyridyl,6-morpholino-3-pyridyl, 3-morpholino-2-pyridyl, 4-morpholino-2-pyridyl,5-morpholino-2-pyridyl, 6-morpholino-2-pyridyl, 2-morpholino-4-pyridyl,3-morpholino-4-pyridyl, 5-morpholino-4-pyridyl, 6-morpholino-4-pyridyl,2-fluoro-3-pyridyl, 4-fluoro-3-pyridyl, 5-fluoro-3-pyridyl,6-fluoro-3-pyridyl, 3-fluoro-2-pyridyl, 4-fluoro-2-pyridyl,5-fluoro-2-pyridyl, 6-fluoro-2-pyridyl, 2-fluoro-4-pyridyl,3-fluoro-4-pyridyl, 5-fluoro-4-pyridyl, 6-fluoro-4-pyridyl,2,4-dimethyl-3-pyridyl, 2,6-dimethyl-3-pyridyl, 5,6-dimethyl-3-pyridyl,4,6-dimethyl-3-pyridyl, 4,5-dimethyl-2-pyridyl, 5,6-dimethyl-2-pyridyl,2,3-dimethyl-4-pyridyl, 2,6-dimethyl-4-pyridyl, 2,4-dimethoxy-3-pyridyl,2,6-dimethoxy-3-pyridyl, 5,6-dimethoxy-3-pyridyl,4,6-dimethoxy-3-pyridyl, 4,5-dimethoxy-2-pyridyl,5,6-dimethoxy-2-pyridyl, 2,3-dimethoxy-4-pyridyl,2,6-dimethoxy-4-pyridyl, 2-chloro-6-methyl-3-pyridyl,6-chloro-2-methyl-3-pyridyl, 2-chloro-6-methoxy-3-pyridyl,6-chloro-2-methoxy-3-pyridyl, 5-methyl-6-chloro-3-pyridyl,5-methoxy-6-chloro-3-pyridyl, 5-ethoxy-6-chloro-3-pyridyl,5-chloro-6-methyl-3-pyridyl, 5-methoxy-6-methyl-3-pyridyl,5-ethoxy-6-methyl-3-pyridyl, 5-chloro-6-methoxy-3-pyridyl,5-chloro-6-ethoxy-3-pyridyl, 2,5,6-trimethyl-3-pyridyl, 2-pyrazinyl,5-methyl-2-pyrazinyl, 6-methyl-2-pyrazinyl, 5-methoxy-2-pyrazinyl,6-methoxy-2-pyrazinyl, 5-ethoxy-2-pyrazinyl, 6-ethoxy-2-pyrazinyl,5-chloro-2-pyrazinyl, 6-chloro-2-pyrazinyl, 3-methyl-2-benzothienyl,4-methyl-2-benzothienyl, 5-methyl-2-benzothienyl,6-methyl-2-benzothienyl, 7-methyl-2-benzothienyl,2-methyl-3-benzothienyl, 4-methyl-3-benzothienyl,5-methyl-3-benzothienyl, 6-methyl-3-benzothienyl,7-methyl-3-benzothienyl, 2-methyl-5-benzothienyl,3-methyl-5-benzothienyl, 4-methyl-5-benzothienyl,6-methyl-5-benzothienyl, 7-methyl-5-benzothienyl,3-methoxy-2-benzothienyl, 4-methoxy-2-benzothienyl,5-methoxy-2-benzothienyl, 6-methoxy-2-benzothienyl,7-methoxy-2-benzothienyl, 2-methoxy-3-benzothienyl,4-methoxy-3-benzothienyl, 5-methoxy-3-benzothienyl,6-methoxy-3-benzothienyl, 7-methoxy-3-benzothienyl,2-methoxy-5-benzothienyl, 3-methoxy-5-benzothienyl,4-methoxy-5-benzothienyl, 6-methoxy-5-benzothienyl,7-methoxy-5-benzothienyl, 3-chloro-2-benzothienyl,4-chloro-2-benzothienyl, 5-chloro-2-benzothienyl,6-chloro-2-benzothienyl, 7-chloro-2-benzothienyl,2-chloro-3-benzothienyl, 4-chloro-3-benzothienyl,5-chloro-3-benzothienyl, 6-chloro-3-benzothienyl,7-chloro-3-benzothienyl, 2-chloro-5-benzothienyl,3-chloro-5-benzothienyl, 4-chloro-5-benzothienyl,6-chloro-5-benzothienyl, 7-chloro-5-benzothienyl,3-fluoro-2-benzothienyl, 4-fluoro-2-benzothienyl,5-fluoro-2-benzothienyl, 6-fluoro-2-benzothienyl,7-fluoro-2-benzothienyl, 2-fluoro-3-benzothienyl,4-fluoro-3-benzothienyl, 5-fluoro-3-benzothienyl,6-fluoro-3-benzothienyl, 7-fluoro-3-benzothienyl,2-fluoro-5-benzothienyl, 3-fluoro-5-benzothienyl,4-fluoro-5-benzothienyl, 6-fluoro-5-benzothienyl,7-fluoro-5-benzothienyl, 3-methyl-2-benzofuryl, 4-methyl-2-benzofuryl,5-methyl-2-benzofuryl, 6-methyl-2-benzofuryl, 7-methyl-2-benzofuryl,2-methyl-3-benzofuryl, 4-methyl-3-benzofuryl, 5-methyl-3-benzofuryl,6-methyl-3-benzofuryl, 7-methyl-3-benzofuryl, 2-methyl-5-benzofuryl,3-methyl-5-benzofuryl, 4-methyl-5-benzofuryl, 6-methyl-5-benzofuryl,7-methyl-5-benzofuryl, 3-methoxy-2-benzofuryl, 4-methoxy-2-benzofuryl,5-methoxy-2-benzofuryl, 6-methoxy-2-benzofuryl, 7-methoxy-2-benzofuryl,2-methoxy-3-benzofuryl, 4-methoxy-3-benzofuryl, 5-methoxy-3-benzofuryl,6-methoxy-3-benzofuryl, 7-methoxy-3-benzofuryl, 2-methoxy-5-benzofuryl,3-methoxy-5-benzofuryl, 4-methoxy-5-benzofuryl, 6-methoxy-5-benzofuryl,7-methoxy-5-benzofuryl, 3-chloro-2-benzofuryl, 4-chloro-2-benzofuryl,5-chloro-2-benzofuryl, 6-chloro-2-benzofuryl, 7-chloro-2-benzofuryl,2-chloro-3-benzofuryl, 4-chloro-3-benzofuryl, 5-chloro-3-benzofuryl,6-chloro-3-benzofuryl, 7-chloro-3-benzofuryl, 2-chloro-5-benzofuryl,3-chloro-5-benzofuryl, 4-chloro-5-benzofuryl, 6-chloro-5-benzofuryl,7-chloro-5-benzofuryl, 3-fluoro-2-benzofuryl, 4-fluoro-2-benzofuryl,5-fluoro-2-benzofuryl, 6-fluoro-2-benzofuryl, 7-fluoro-2-benzofuryl,2-fluoro-3-benzofuryl, 4-fluoro-3-benzofuryl, 5-fluoro-3-benzofuryl,6-fluoro-3-benzofuryl, 7-fluoro-3-benzofuryl, 2-fluoro-5-benzofuryl,3-fluoro-5-benzofuryl, 4-fluoro-5-benzofuryl, 6-fluoro-5-benzofuryl,7-fluoro-5-benzofuryl, 1-methyl-2-indolyl, 3-methyl-2-indolyl,4-methyl-2-indolyl, 5-methyl-2-indolyl, 6-methyl-2-indolyl,7-methyl-2-indolyl, 1-methyl-3-indolyl, 2-methyl-3-indolyl,4-methyl-3-indolyl, 5-methyl-3-indolyl, 6-methyl-3-indolyl,7-methyl-3-indolyl, 1-methyl-5-indolyl, 2-methyl-5-indolyl,3-methyl-5-indolyl, 4-methyl-5-indolyl, 6-methyl-5-indolyl,7-methyl-5-indolyl, 3-methoxy-2-indolyl, 4-methoxy-2-indolyl,5-methoxy-2-indolyl, 6-methoxy-2-indolyl, 7-methoxy-2-indolyl,2-methoxy-3-indolyl, 4-methoxy-3-indolyl, 5-methoxy-3-indolyl,6-methoxy-3-indolyl, 7-methoxy-3-indolyl, 2-methoxy-5-indolyl,3-methoxy-5-indolyl, 4-methoxy-5-indolyl, 6-methoxy-5-indolyl,7-methoxy-5-indolyl, 3-chloro-2-indolyl, 4-chloro-2-indolyl,5-chloro-2-indolyl, 6-chloro-2-indolyl, 7-chloro-2-indolyl,2-chloro-3-indolyl, 4-chloro-3-indolyl, 5-chloro-3-indolyl,6-chloro-3-indolyl, 7-chloro-3-indolyl, 2-chloro-5-indolyl,3-chloro-5-indolyl, 4-chloro-5-indolyl, 6-chloro-5-indolyl,7-chloro-5-indolyl, 3-fluoro-2-indolyl, 4-fluoro-2-indolyl,5-fluoro-2-indolyl, 6-fluoro-2-indolyl, 7-fluoro-2-indolyl,2-fluoro-3-indolyl, 4-fluoro-3-indolyl, 5-fluoro-3-indolyl,6-fluoro-3-indolyl, 7-fluoro-3-indolyl, 2-fluoro-5-indolyl,3-fluoro-5-indolyl, 4-fluoro-5-indolyl, 6-fluoro-5-indolyl,7-fluoro-5-indolyl, 3-methyl-2-quinolyl, 4-methyl-2-quinolyl,5-methyl-2-quinolyl, 6-methyl-2-quinolyl, 7-methyl-2-quinolyl,8-methyl-2-quinolyl, 2-methyl-4-quinolyl, 3-methyl-4-quinolyl,5-methyl-4-quinolyl, 6-methyl-4-quinolyl, 7-methyl-4-quinolyl,8-methyl-4-quinolyl, 2-methyl-6-quinolyl, 3-methyl-6-quinolyl,4-methyl-6-quinolyl, 5-methyl-6-quinolyl, 7-methyl-6-quinolyl,8-methyl-6-quinolyl, 3-methoxy-2-quinolyl, 4-methoxy-2-quinolyl,5-methoxy-2-quinolyl, 6-methoxy-2-quinolyl, 7-methoxy-2-quinolyl,8-methoxy-2-quinolyl, 2-methoxy-4-quinolyl, 3-methoxy-4-quinolyl,5-methoxy-4-quinolyl, 6-methoxy-4-quinolyl, 7-methoxy-4-quinolyl,8-methoxy-4-quinolyl, 2-methoxy-6-quinolyl, 3-methoxy-6-quinolyl,4-methoxy-6-quinolyl, 5-methoxy-6-quinolyl, 7-methoxy-6-quinolyl,8-methoxy-6-quinolyl, 3-chloro-2-quinolyl, 4-chloro-2-quinolyl,5-chloro-2-quinolyl, 6-chloro-2-quinolyl, 7-chloro-2-quinolyl,8-chloro-2-quinolyl, 2-chloro-4-quinolyl, 3-chloro-4-quinolyl,5-chloro-4-quinolyl, 6-chloro-4-quinolyl, 7-chloro-4-quinolyl,8-chloro-4-quinolyl, 2-chloro-6-quinolyl, 3-chloro-6-quinolyl,4-chloro-6-quinolyl, 5-chloro-6-quinolyl, 7-chloro-6-quinolyl,8-chloro-6-quinolyl, 3-fluoro-2-quinolyl, 4-fluoro-2-quinolyl,5-fluoro-2-quinolyl, 6-fluoro-2-quinolyl, 7-fluoro-2-quinolyl,8-fluoro-2-quinolyl, 2-fluoro-4-quinolyl, 3-fluoro-4-quinolyl,5-fluoro-4-quinolyl, 6-fluoro-4-quinolyl, 7-fluoro-4-quinolyl,8-fluoro-4-quinolyl, 2-fluoro-6-quinolyl, 3-fluoro-6-quinolyl,4-fluoro-6-quinolyl, 5-fluoro-6-quinolyl, 7-fluoro-6-quinolyl, and8-fluoro-6-quinolyl.

In general formula (I), examples of further preferable X include NH andan oxygen atom, with NH being particularly preferable.

In general formula (I), examples of further preferable R¹ include C₁₋₆alkyl, C₂₋₆ alkenyl, and C₂₋₆ alkynyl. Specific examples thereof includemethyl, ethyl, propyl, isopropyl, butyl, 2-butyl, pentyl, 2-pentyl,hexyl, 2-hexyl, vinyl, propenyl, butenyl, butynyl, and pentenyl. Amongthem, C₃₋₅ alkyl, C₃₋₅ alkenyl, and C₃₋₅ alkynyl, more specifically,propyl, isopropyl, butyl, 2-butyl, pentyl, 2-pentyl, propenyl, butenyl,butynyl, and pentenyl are further preferable, with propyl, butyl, andpentyl being particularly preferable.

In general formula (I), examples of further preferable R² includehydroxyl, acetyloxy, propionyloxy, methoxycarbonyloxy,ethoxycarbonyloxy, propoxycarbonyloxy, and butoxycarbonyloxy, withhydroxyl, methoxycarbonyloxy, and ethoxycarbonyloxy being particularlypreferable.

In general formula (I), examples of further preferable Y include asubstituted or unsubstituted pyridine ring (e.g., 2-pyridyl, 3-pyridyl,and 4-pyridyl) and a pyrazine ring (e.g., 2-pyrazinyl and 3-pyrazinyl),with 3-pyridyl being particularly preferable. Examples of furtherpreferable Y having a substituent include 2-methyl-3-pyridyl,6-methyl-3-pyridyl, 2-ethyl-3-pyridyl, 6-ethyl-3-pyridyl,2-methoxy-3-pyridyl, 6-methoxy-3-pyridyl, 2-ethoxy-3-pyridyl,6-ethoxy-3-pyridyl, 2-chloro-3-pyridyl, 6-chloro-3-pyridyl,6-dimethylamino-3-pyridyl, 6-(1-pyrrolidinyl)-3-pyridyl,6-piperidino-3-pyridyl, 6-morpholino-3-pyridyl, 6-methylthio-3-pyridyl,5,6-dimethyl-3-pyridyl, 5,6-dimethoxy-3-pyridyl, 2,6-dichloro-3-pyridyl,5,6-dichloro-3-pyridyl, and 5-chloro-6-methoxy-3-pyridyl. Among them,3-pyridyl, 6-methyl-3-pyridyl, 6-methoxy-3-pyridyl, 6-ethoxy-3-pyridyl,6-chloro-3-pyridyl, 6-(1-pyrrolidinyl)-3-pyridyl,6-morpholino-3-pyridyl, 2-methyl-3-pyridyl, 2-methoxy-3-pyridyl, and2-chloro-3-pyridyl are particularly preferable.

Specific examples of the compounds in the scope of the present inventioninclude the following.

TABLE 1 X R¹ R² Y NH propyl OH 2-pyridyl NH propyl OH 3-pyridyl NHpropyl OH 4-pyridyl NH propyl OH 2-methyl-3-pyridyl NH propyl OH4-methyl-3-pyridyl NH propyl OH 5-methyl-3-pyridyl NH propyl OH6-methyl-3-pyridyl NH propyl OH 2-ethyl-3-pyridyl NH propyl OH4-ethyl-3-pyridyl NH propyl OH 5-ethyl-3-pyridyl NH propyl OH6-ethyl-3-pyridyl NH propyl OH 2-methoxy-3-pyridyl NH propyl OH4-methoxy-3-pyridyl NH propyl OH 5-methoxy-3-pyridyl NH propyl OH6-methoxy-3-pyridyl NH propyl OH 2-ethoxy-3-pyridyl NH propyl OH4-ethoxy-3-pyridyl NH propyl OH 5-ethoxy-3-pyridyl NH propyl OH6-ethoxy-3-pyridyl NH propyl OH 2-chloro-3-pyridyl NH propyl OH4-chloro-3-pyridyl NH propyl OH 5-chloro-3-pyridyl NH propyl OH6-chloro-3-pyridyl NH propyl OH 2-fluoro-3-pyridyl NH propyl OH4-fluoro-3-pyridyl NH propyl OH 5-fluoro-3-pyridyl NH propyl OH6-fluoro-3-pyridyl NH propyl OH 2-dimethylamino-3-pyridyl NH propyl OH4-dimethylamino-3-pyridyl NH propyl OH 5-dimethylamino-3-pyridyl NHpropyl OH 6-dimethylamino-3-pyridyl NH propyl OH2-(1-pyrrolidinyl)-3-pyridyl NH propyl OH 3-(1-pyrrolidinyl)-3-pyridylNH propyl OH 5-(1-pyrrolidinyl)-3-pyridyl NH propyl OH6-(1-pyrrolidinyl)-3-pyridyl NH propyl OH 2-piperidino-3-pyridyl NHpropyl OH 4-piperidino-3-pyridyl NH propyl OH 5-piperidino-3-pyridyl NHpropyl OH 6-piperidino-3-pyridyl NH propyl OH 2-morpholino-3-pyridyl NHpropyl OH 4-morpholino-3-pyridyl NH propyl OH 5-morpholino-3-pyridyl NHpropyl OH 6-morpholino-3-pyridyl NH propyl OH 2-hydroxy-3-pyridyl NHpropyl OH 4-hydroxy-3-pyridyl NH propyl OH 5-hydroxy-3-pyridyl NH propylOH 6-hydroxy-3-pyridyl NH propyl OH 2-mercapto-3-pyridyl NH propyl OH4-mercapto-3-pyridyl NH propyl OH 5-mercapto-3-pyridyl NH propyl OH6-mercapto-3-pyridyl NH propyl OH 2-methylthio-3-pyridyl NH propyl OH4-methylthio-3-pyridyl NH propyl OH 5-methylthio-3-pyridyl NH propyl OH6-methylthio-3-pyridyl NH propyl OH 2,6-dimethyl-3-pyridyl NH propyl OH5,6-dimethyl-3-pyridyl NH propyl OH 2,6-diethyl-3-pyridyl NH propyl OH5,6-diethyl-3-pyridyl NH propyl OH 2,6-dimethoxy-3-pyridyl NH propyl OH5,6-dimethoxy-3-pyridyl NH propyl OH 2,6-diethoxy-3-pyridyl NH propyl OH5,6-diethoxy-3-pyridyl NH propyl OH 2,6-dichloro-3-pyridyl NH propyl OH5,6-dichloro-3-pyridyl NH propyl OH 5-chloro-6-methoxy-3-pyridyl NHpropyl OH 5-chloro-6-ethoxy-3-pyridyl NH propyl OH2-chloro-6-methyl-3-pyridyl NH propyl OH 6-chloro-2-methyl-3-pyridyl NHpropyl OH 2-methyl-4-pyridyl NH propyl OH 2-ethyl-4-pyridyl NH propyl OH2-methoxy-4-pyridyl NH propyl OH 2-ethoxy-4-pyridyl NH propyl OH2-chloro-4-pyridyl NH propyl OH 2-dimethylamino-4-pyridyl NH propyl OH2-(1-pyrrolidinyl)-4-pyridyl NH propyl OH 2-piperidino-4-pyridyl NHpropyl OH 2-morpholino-4-pyridyl NH propyl OH 2-methylthio-4-pyridyl NHpropyl OH 2-pyrazinyl NH propyl OH 5-methyl-2-pyrazinyl NH propyl OH5-ethyl-2-pyrazinyl NH propyl OH 5-methoxy-2-pyrazinyl NH propyl OH5-ethoxy-2-pyrazinyl NH propyl OH 5-chloro-2-pyrazinyl NH propyl OH6-methyl-2-pyrazinyl NH propyl OH 6-methoxy-2-pyrazinyl NH propyl OH6-chloro-2-pyrazinyl NH propyl OCOOMe 2-pyridyl NH propyl OCOOMe3-pyridyl NH propyl OCOOMe 4-pyridyl NH propyl OCOOMe 2-methyl-3-pyridylNH propyl OCOOMe 4-methyl-3-pyridyl NH propyl OCOOMe 5-methyl-3-pyridylNH propyl OCOOMe 6-methyl-3-pyridyl NH propyl OCOOMe 2-ethyl-3-pyridylNH propyl OCOOMe 4-ethyl-3-pyridyl NH propyl OCOOMe 5-ethyl-3-pyridyl NHpropyl OCOOMe 6-ethyl-3-pyridyl NH propyl OCOOMe 2-methoxy-3-pyridyl NHpropyl OCOOMe 4-methoxy-3-pyridyl NH propyl OCOOMe 5-methoxy-3-pyridylNH propyl OCOOMe 6-methoxy-3-pyridyl NH propyl OCOOMe 2-ethoxy-3-pyridylNH propyl OCOOMe 4-ethoxy-3-pyridyl NH propyl OCOOMe 5-ethoxy-3-pyridylNH propyl OCOOMe 6-ethoxy-3-pyridyl NH propyl OCOOMe 2-chloro-3-pyridylNH propyl OCOOMe 4-chloro-3-pyridyl NH propyl OCOOMe 5-chloro-3-pyridylNH propyl OCOOMe 6-chloro-3-pyridyl NH propyl OCOOMe 2-fluoro-3-pyridylNH propyl OCOOMe 4-fluoro-3-pyridyl NH propyl OCOOMe 5-fluoro-3-pyridylNH propyl OCOOMe 6-fluoro-3-pyrjdyl NH propyl OCOOMe2-dimethylamino-3-pyridyl NH propyl OCOOMe 4-dimethylamino-3-pyridy1 NHpropyl OCOOMe 5-dimethylamino-3-pyridyl NH propyl OCOOMe6-dimethylamino-3-pyridyl NH propyl OCOOMe 2-(1-pyrrolidinyl)-3-pyridylNH propyl OCOOMe 3-(1-pyrrolidinyl)-3-pyridyl NH propyl OCOOMe5-(1-pyrrolidinyl)-3-pyridyl NH propyl OCOOMe6-(1-pyrrolidinyl)-3-pyridyl NH propyl OCOOMe 2-piperidino-3-pyridyl NHpropyl OCOOMe 4-piperidino-3-pyridyl NH propyl OCOOMe5-piperidino-3-pyridyl NH propyl OCOOMe 6-piperidino-3-pyridyl NH propylOCOOMe 2-morpholino-3-pyridyl NH propyl OCOOMe 4-morpholino-3-pyridyl NHpropyl OCOOMe 5-morpholino-3-pyridyl NH propyl OCOOMe6-morpholino-3-pyridyl NH propyl OCOOMe 2-hydroxy-3-pyridyl NH propylOCOOMe 4-hydroxy-3-pyridyl NH propyl OCOOMe 5-hydroxy-3-pyridyl NHpropyl OCOOMe 6-hydroxy-3-pyridyl NH propyl OCOOMe 2-mercapto-3-pyridylNH propyl OCOOMe 4-mercapto-3-pyridyl NH propyl OCOOMe5-mercapto-3-pyridyl NH propyl OCOOMe 6-mercapto-3-pyridyl NH propylOCOOMe 2-methylthio-3-pyridyl NH propyl OCOOMe 4-methylthio-3-pyridyl NHpropyl OCOOMe 5-methylthio-3-pyridyl NH propyl OCOOMe6-methylthio-3-pyridyl NH propyl OCOOMe 2,6-dimethyl-3-pyridyl NH propylOCOOMe 5,6-dimethyl-3-pyridyl NH propyl OCOOMe 2,6-diethyl-3-pyridyl NHpropyl OCOOMe 5,6-diethyl-3-pyridyl NH propyl OCOOMe2,6-dimethoxy-3-pyridyl NH propyl OCOOMe 5,6-dimethoxy-3-pyridyl NHpropyl OCOOMe 2,6-diethoxy-3-pyridyl NH propyl OCOOMe5,6-diethoxy-3-pyridyl NH propyl OCOOMe 2,6-dichloro-3-pyridyl NH propylOCOOMe 5,6-dichloro-3-pyridyl NH propyl OCOOMe5-chloro-6-methoxy-3-pyridyl NH propyl OCOOMe5-chloro-6-ethoxy-3-pyridyl NH propyl OCOOMe 2-chloro-6-methyl-3-pyridylNH propyl OCOOMe 6-chloro-2-methyl-3-pyridyl NH propyl OCOOMe2-methyl-4-pyridyl NH propyl OCOOMe 2-ethyl-4-pyridyl NH propyl OCOOMe2-methoxy-4-pyridyl NH propyl OCOOMe 2-ethoxy-4-pyridyI NH propyl OCOOMe2-chloro-4-pyridyl NH propyl OCOOMe 2-dimethylamino-4-pyridyl NH propylOCOOMe 2-(1-pyrrolidinyl)-4-pyridyl NH propyl OCOOMe2-piperidino-4-pyridyl NH propyl OCOOMe 2-morpholino-4-pyridyl NH propylOCOOMe 2-methylthio-4-pyridyl NH propyl OCOOMe 2-pyrazinyl NH propylOCOOMe 5-methyl-2-pyrazinyl NH propyl OCOOMe 5-ethyl-2-pyrazinyl NHpropyl OCOOMe 5-methoxy-2-pyrazinyl NH propyl OCOOMe5-ethoxy-2-pyrazinyl NH propyl OCOOMe 5-chloro-2-pyrazinyl NH propylOCOOMe 6-methyl-2-pyrazinyl NH propyl OCOOMe 6-methoxy-2-pyrazinyl NHpropyl OCOOMe 6-chloro-2-pyrazinyl NH propyl OCOOEt 2-pyridyl NH propylOCOOEt 3-pyridyl NH propyl OCOOEt 4-pyridyl NH propyl OCOOEt2-methyl-3-pyridyl NH propyl OCOOEt 4-methyl-3-pyridyl NH propyl OCOOEt5-methyl-3-pyridyl NH propyl OCOOEt 6-methyl-3-pyridyl NH propyl OCOOEt2-ethyl-3-pyridyl NH propyl OCOOEt 4-ethyl-3-pyridyl NH propyl OCOOEt5-ethyl-3-pyridyl NH propyl OCOOEt 6-ethyl-3-pyridyl NH propyl OCOOEt2-methoxy-3-pyridyl NH propyl OCOOEt 4-methoxy-3-pyridyl NH propylOCOOEt 5-methoxy-3-pyridyl NH propyl OCOOEt 6-methoxy-3-pyridyl NHpropyl OCOOEt 2-ethoxy-3-pyridyl NH propyl OCOOEt 4-ethoxy-3-pyridyl NHpropyl OCOOEt 5-ethoxy-3-pyridyl NH propyl OCOOEt 6-ethoxy-3-pyridyl NHpropyl OCOOEt 2-chloro-3-pyridyl NH propyl OCOOEt 4-chloro-3-pyridyl NHpropyl OCOOEt 5-chloro-3-pyridyl NH propyl OCOOEt 6-chloro-3-pyridyl NHpropyl OCOOEt 2-fluoro-3-pyridyl NH propyl OCOOEt 4-fluoro-3-pyridyl NHpropyl OCOOEt 5-fluoro-3-pyridyl NH propyl OCOOEt 6-fluoro-3-pyridyl NHpropyl OCOOEt 2-dimethylamino-3-pyridyl NH propyl OCOOEt4-dimethylamino-3-pyridyl NH propyl OCOOEt 5-dimethylamino-3-pyridyl NHpropyl OCOOEt 6-dimethylamino-3-pyridyl NH propyl OCOOEt2-(1-pyrrolidinyl)-3-pyridyl NH propyl OCOOEt3-(1-pyrrolidinyl)-3-pyridyl NH propyl OCOOEt5-(1-pyrrolidinyl)-3-pyridyl NH propyl OCOOEt6-(1-pyrrolidinyl)-3-pyridyl NH propyl OCOOEt 2-piperidino-3-pyridyl NHpropyl OCOOEt 4-piperidino-3-pyridyl NH propyl OCOOEt5-piperidino-3-pyridyl NH propyl OCOOEt 6-piperidino-3-pyridyl NH propylOCOOEt 2-morpholino-3-pyridyl NH propyl OCOOEt 4-morpholino-3-pyridyl NHpropyl OCOOEt 5-morpholino-3-pyridyl NH propyl OCOOEt6-morpholino-3-pyridyl NH propyl OCOOEt 2-hydroxy-3-pyridyl NH propylOCOOEt 4-hydroxy-3-pyridyl NH propyl OCOOEt 5-hydroxy-3-pyridyl NHpropyl OCOOEt 6-hydroxy-3-pyridyl NH propyl OCOOEt 2-mercapto-3-pyridylNH propyl OCOOEt 4-mercapto-3-pyridyl NH propyl OCOOEt5-mercapto-3-pyridyl NH propyl OCOOEt 6-mercapto-3-pyridyl NH propylOCOOEt 2-methylthio-3-pyridyl NH propyl OCOOEt 4-methylthio-3-pyridyl NHpropyl OCOOEt 5-methylthio-3-pyridyl NH propyl OCOOEt6-methylthio-3-pyridyl NH propyl OCOOEt 2,6-dimethyl-3-pyridyl NH propylOCOOEt 5,6-dimethyl-3-pyridyl NH propyl OCOOEt 2,6-diethyl-3-pyridyl NHpropyl OCOOEt 5,6-diethyl-3-pyridyl NH propyl OCOOEt2,6-dimethoxy-3-pyridyl NH propyl OCOOEt 5,6-dimethoxy-3-pyridyl NHpropyl OCOOEt 2,6-diethoxy-3-pyridyl NH propyl OCOOEt5,6-diethoxy-3-pyridyl NH propyl OCOOEt 2,6-dichloro-3-pyridyl NH propylOCOOEt 5,6-dichloro-3-pyridyl NH propyl OCOOEt5-chloro-6-methoxy-3-pyridyl NH propyl OCOOEt5-chloro-6-ethoxy-3-pyridyl NH propyl OCOOEt 2-chloro-6-methyl-3-pyridylNH propyl OCOOEt 6-chloro-2-methyl-3-pyridyl NH propyl OCOOEt2-methyl-4-pyridyl NH propyl OCOOEt 2-ethyl-4-pyridyl NH propyl OCOOEt2-methoxy-4-pyridyl NH propyl OCOOEt 2-ethoxy-4-pyridyl NH propyl OCOOEt2-chloro-4-pyridyl NH propyl OCOOEt 2-dimethylamino-4-pyridyl NH propylOCOOEt 2-(1-pyrrolidinyl)-4-pyridyl NH propyl OCOOEt2-piperidino-4-pyridyl NH propyl OCOOEt 2-morpholino-4-pyridyl NH propylOCOOEt 2-methylthio-4-pyridyl NH propyl OCOOEt 2-pyrazinyl NH propylOCOOEt 5-methyl-2-pyrazinyl NH propyl OCOOEt 5-ethyl-2-pyrazinyl NHpropyl OCOOEt 5-methoxy-2-pyrazinyl NH propyl OCOOEt5-ethoxy-2-pyrazinyl NH propyl OCOOEt 5-chloro-2-pyrazinyl NH propylOCOOEt 6-methyl-2-pyrazinyl NH propyl OCOOEt 6-methoxy-2-pyrazinyl NHpropyl OCOOEt 6-chloro-2-pyrazinyl NH n-butyl OH 2-pyridyl NH n-butyl OH3-pyridyl NH n-butyl OH 4-pyridyl NH n-butyl OH 2-methyl-3-pyridyl NHn-butyl OH 4-methyl-3-pyridyl NH n-butyl OH 5-methyl-3-pyridyl NHn-butyl OH 6-methyl-3-pyridyl NH n-butyl OH 2-ethyl-3-pyridyl NH n-butylOH 4-ethyl-3-pyridyl NH n-butyl OH 5-ethyl-3-pyridyl NH n-butyl OH6-ethyl-3-pyridyl NH n-butyl OH 2-methoxy-3-pyridyl NH n-butyl OH4-methoxy-3-pyridyl NH n-butyl OH 5-methoxy-3-pyridyl NH n-butyl OH6-methoxy-3-pyridyl NH n-butyl OH 2-ethoxy-3-pyridyl NH n-butyl OH4-ethoxy-3-pyridyl NH n-butyl OH 5-ethoxy-3-pyridyl NH n-butyl OH6-ethoxy-3-pyridyl NH n-butyl OH 2-chloro-3-pyridyl NH n-butyl OH4-chloro-3-pyridyl NH n-butyl OH 5-chloro-3-pyridyl NH n-butyl OH6-chloro-3-pyridyl NH n-butyl OH 2-fluoro-3-pyridyl NH n-butyl OH4-fluoro-3-pyridyl NH n-butyl OH 5-fluoro-3-pyridyl NH n-butyl OH6-fluoro-3-pyridyl NH n-butyl OH 2-dimethylamino-3-pyridyl NH n-butyl OH4-dimethylamino-3-pyridyl NH n-butyl OH 5-dimethylamino-3-pyridyl NHn-butyl OH 6-dimethylamino-3-pyridyl NH n-butyl OH2-(1-pyrrolidinyl)-3-pyridyl NH n-butyl OH 3-(1-pyrrolidinyl)-3-pyridylNH n-butyl OH 5-(1-pyrrolidinyl)-3-pyridyl NH n-butyl OH6-(1-pyrrolidinyl)-3-pyridyl NH n-butyl OH 2-piperidino-3-pyridyl NHn-butyl OH 4-piperidino-3-pyridyl NH n-butyl OH 5-piperidino-3-pyridylNH n-butyl OH 6-piperidino-3-pyridyl NH n-butyl OH2-morpholino-3-pyridyl NH n-butyl OH 4-morpholino-3-pyridyl NH n-butylOH 5-morpholino-3-pyridyl NH n-butyl OH 6-morpholino-3-pyridyl NHn-butyl OH 2-hydroxy-3-pyridyl NH n-butyl OH 4-hydroxy-3-pyridyl NHn-butyl OH 5-hydroxy-3-pyridyl NH n-butyl OH 6-hydroxy-3-pyridyl NHn-butyl OH 2-mercapto-3-pyridyl NH n-butyl OH 4-mercapto-3-pyridyl NHn-butyl OH 5-mercapto-3-pyridyl NH n-butyl OH 6-mercapto-3-pyridyl NHn-butyl OH 2-methylthio-3-pyridyl NH n-butyl OH 4-methylthio-3-pyridylNH n-butyl OH 5-methylthio-3-pyridyl NH n-butyl OH6-methylthio-3-pyridyl NH n-butyl OH 2,6-dimethyl-3-pyridyl NH n-butylOH 5,6-dimethyl-3-pyridyl NH n-butyl OH 2,6-diethyl-3-pyridyl NH n-butylOH 5,6-diethyl-3-pyridyl NH n-butyl OH 2,6-dimethoxy-3-pyridyl NHn-butyl OH 5,6-dimethoxy-3-pyridyl NH n-butyl OH 2,6-diethoxy-3-pyridylNH n-butyl OH 5,6-diethoxy-3-pyridyl NH n-butyl OH2,6-dichloro-3-pyridyl NH n-butyl OH 5,6-dichloro-3-pyridyl NH n-butylOH 5-chloro-6-methoxy-3-pyridyl NH n-butyl OH5-chloro-6-ethoxy-3-pyridyl NH n-butyl OH 2-chloro-6-methyl-3-pyridyl NHn-butyl OH 6-chloro-2-methyl-3-pyridyl NH n-butyl OH 2-methyl-4-pyridylNH n-butyl OH 2-ethyl-4-pyridyl NH n-butyl OH 2-methoxy-4-pyridyl NHn-butyl OH 2-ethoxy-4-pyridyl NH n-butyl OH 2-chloro-4-pyridyl NHn-butyl OH 2-dimethylamino-4-pyridyl NH n-butyl OH2-(1-pyrrolidinyl)-4-pyridyl NH n-butyl OH 2-piperidino-4-pyridyl NHn-butyl OH 2-morpholino-4-pyridyl NH n-butyl OH 2-methylthio-4-pyridylNH n-butyl OH 2-pyrazinyl NH n-butyl OH 5-methyl-2-pyrazinyl NH n-butylOH 5-ethyl-2-pyrazinyl NH n-butyl OH 5-methoxy-2-pyrazinyl NH n-butyl OH5-ethoxy-2-pyrazinyl NH n-butyl OH 5-chloro-2-pyrazinyl NH n-butyl OH6-methyl-2-pyrazinyl NH n-butyl OH 6-methoxy-2-pyrazinyl NH n-butyl OH6-chloro-2-pyrazinyl NH n-butyl OCOOMe 2-pyridyl NH n-butyl OCOOMe3-pyridyl NH n-butyl OCOOMe 4-pyridyl NH n-butyl OCOOMe2-methyl-3-pyridyl NH n-butyl OCOOMe 4-methyl-3-pyridyl NH n-butylOCOOMe 5-methyl-3-pyridyl NH n-butyl OCOOMe 6-methyl-3-pyridyl NHn-butyl OCOOMe 2-ethyl-3-pyridyl NH n-butyl OCOOMe 4-ethyl-3-pyridyl NHn-butyl OCOOMe 5-ethyl-3-pyridyl NH n-butyl OCOOMe 6-ethyl-3-pyridyl NHn-butyl OCOOMe 2-methoxy-3-pyridyl NH n-butyl OCOOMe 4-methoxy-3-pyridylNH n-butyl OCOOMe 5-methoxy-3-pyridyl NH n-butyl OCOOMe6-methoxy-3-pyridyl NH n-butyl OCOOMe 2-ethoxy-3-pyridyl NH n-butylOCOOMe 4-ethoxy-3-pyridyl NH n-butyl OCOOMe 5-ethoxy-3-pyridyl NHn-butyl OCOOMe 6-ethoxy-3-pyridyl NH n-butyl OCOOMe 2-chloro-3-pyridylNH n-butyl OCOOMe 4-chloro-3-pyridyl NH n-butyl OCOOMe5-chloro-3-pyridyl NH n-butyl OCOOMe 6-chloro-3-pyridyl NH n-butylOCOOMe 2-fluoro-3-pyridyl NH n-butyl OCOOMe 4-fluoro-3-pyridyl NHn-butyl OCOOMe 5-fluoro-3-pyridyl NH n-butyl OCOOMe 6-fluoro-3-pyridylNH n-butyl OCOOMe 2-dimethylamino-3-pyridyl NH n-butyl OCOOMe4-dimethylamino-3-pyridyl NH n-butyl OCOOMe 5-dimethylamino-3-pyridyl NHn-butyl OCOOMe 6-dimethylamino-3-pyridyl NH n-butyl OCOOMe2-(1-pyrrolidinyl)-3-pyridyl NH n-butyl OCOOMe3-(1-pyrrolidinyl)-3-pyridyl NH n-butyl OCOOMe5-(1-pyrrolidinyl)-3-pyridyl NH n-butyl OCOOMe6-(1-pyrrolidinyl)-3-pyridyl NH n-butyl OCOOMe 2-piperidino-3-pyridyl NHn-butyl OCOOMe 4-piperidino-3-pyridyl NH n-butyl OCOOMe5-piperidino-3-pyridyl NH n-butyl OCOOMe 6-piperidino-3-pyridyl NHn-butyl OCOOMe 2-morpholino-3-pyridyl NH n-butyl OCOOMe4-morpholino-3-pyridyl NH n-butyl OCOOMe 5-morpholino-3-pyridyl NHn-butyl OCOOMe 6-morpholino-3-pyridyl NH n-butyl OCOOMe2-hydroxy-3-pyridyl NH n-butyl OCOOMe 4-hydroxy-3-pyridyl NH n-butylOCOOMe 5-hydroxy-3-pyridyl NH n-butyl OCOOMe 6-hydroxy-3-pyridyl NHn-butyl OCOOMe 2-mercapto-3-pyridyl NH n-butyl OCOOMe4-mercapto-3-pyridyl NH n-butyl OCOOMe 5-mercapto-3-pyridyl NH n-butylOCOOMe 6-mercapto-3-pyridyl NH n-butyl OCOOMe 2-methylthio-3-pyridyl NHn-butyl OCOOMe 4-methylthio-3-pyridyl NH n-butyl OCOOMe5-methylthio-3-pyridyl NH n-butyl OCOOMe 6-methylthio-3-pyridyl NHn-butyl OCOOMe 2,6-dimethyl-3-pyridyl NH n-butyl OCOOMe5,6-dimethyl-3-pyridyl NH n-butyl OCOOMe 2,6-diethyl-3-pyridyl NHn-butyl OCOOMe 5,6-diethyl-3-pyridyl NH n-butyl OCOOMe2,6-dimethoxy-3-pyridyl NH n-butyl OCOOMe 5,6-dimethoxy-3-pyridyl NHn-butyl OCOOMe 2,6-diethoxy-3-pyridyl NH n-butyl OCOOMe5,6-diethoxy-3-pyridyl NH n-butyl OCOOMe 2,6-dichloro-3-pyridyl NHn-butyl OCOOMe 5,6-dichloro-3-pyridyl NH n-butyl OCOOMe5-chloro-6-methoxy-3-pyridyl NH n-butyl OCOOMe5-chloro-6-ethoxy-3-pyridyl NH n-butyl OCOOMe2-chloro-6-methyl-3-pyridyl NH n-butyl OCOOMe6-chloro-2-methyl-3-pyridyl NH n-butyl OCOOMe 2-methyl-4-pyridyl NHn-butyl OCOOMe 2-ethyl-4-pyridyl NH n-butyl OCOOMe 2-methoxy-4-pyridylNH n-butyl OCOOMe 2-ethoxy-4-pyridyl NH n-butyl OCOOMe2-chloro-4-pyridyl NH n-butyl OCOOMe 2-dimethylamino-4-pyridyl NHn-butyl OCOOMe 2-(1-pyrrolidinyl)-4-pyridyl NH n-butyl OCOOMe2-piperidino-4-pyridyl NH n-butyl OCOOMe 2-morpholino-4-pyridyl NHn-butyl OCOOMe 2-methylthio-4-pyridyl NH n-butyl OCOOMe 2-pyrazinyl NHn-butyl OCOOMe 5-methyl-2-pyrazinyl NH n-butyl OCOOMe5-ethyl-2-pyrazinyl NH n-butyl OCOOMe 5-methoxy-2-pyrazinyl NH n-butylOCOOMe 5-ethoxy-2-pyrazinyl NH n-butyl OCOOMe 5-chloro-2-pyrazinyl NHn-butyl OCOOMe 6-methyl-2-pyrazinyl NH n-butyl OCOOMe6-methoxy-2-pyrazinyl NH n-butyl OCOOMe 6-chloro-2-pyrazinyl NH n-butylOCOOEt 2-pyridyl NH n-butyl OCOOEt 3-pyridyl NH n-butyl OCOOEt 4-pyridylNH n-butyl OCOOEt 2-methyl-3-pyridyl NH n-butyl OCOOEt4-methyl-3-pyridyl NH n-butyl OCOOEt 5-methyl-3-pyridyl NH n-butylOCOOEt 6-methyl-3-pyridyl NH n-butyl OCOOEt 2-ethyl-3-pyridyl NH n-butylOCOOEt 4-ethyl-3-pyridyl NH n-butyl OCOOEt 5-ethyl-3-pyridyl NH n-butylOCOOEt 6-ethyl-3-pyridyl NH n-butyl OCOOEt 2-methoxy-3-pyridyl NHn-butyl OCOOEt 4-methoxy-3-pyridyl NH n-butyl OCOOEt 5-methoxy-3-pyridylNH n-butyl OCOOEt 6-methoxy-3-pyridyl NH n-butyl OCOOEt2-ethoxy-3-pyridyl NH n-butyl OCOOEt 4-ethoxy-3-pyridyl NH n-butylOCOOEt 5-ethoxy-3-pyridyl NH n-butyl OCOOEt 6-ethoxy-3-pyridyl NHn-butyl OCOOEt 2-chloro-3-pyridyl NH n-butyl OCOOEt 4-chloro-3-pyridylNH n-butyl OCOOEt 5-chloro-3-pyridyl NH n-butyl OCOOEt6-chloro-3-pyridyl NH n-butyl OCOOEt 2-fluoro-3-pyridyl NH n-butylOCOOEt 4-fluoro-3-pyridyl NH n-butyl OCOOEt 5-fluoro-3-pyridyl NHn-butyl OCOOEt 6-fluoro-3-pyridyl NH n-butyl OCOOEt2-dimethylamino-3-pyridyl NH n-butyl OCOOEt 4-dimethylamino-3-pyridyl NHn-butyl OCOOEt 5-dimethylamino-3-pyridyl NH n-butyl OCOOEt6-dimethylamino-3-pyridyl NH n-butyl OCOOEt 2-(1-pyrrolidinyl)-3-pyridylNH n-butyl OCOOEt 3-(1-pyrrolidinyl)-3-pyridyl NH n-butyl OCOOEt5-(1-pyrrolidinyl)-3-pyridyl NH n-butyl OCOOEt6-(1-pyrrolidinyl)-3-pyridyl NH n-butyl OCOOEt 2-piperidino-3-pyridyl NHn-butyl OCOOEt 4-piperidino-3-pyridyl NH n-butyl OCOOEt5-piperidino-3-pyridyl NH n-butyl OCOOEt 6-piperidino-3-pyridyl NHn-butyl OCOOEt 2-morpholino-3-pyridyl NH n-butyl OCOOEt4-morpholino-3-pyridyl NH n-butyl OCOOEt 5-morpholino-3-pyridyl NHn-butyl OCOOEt 6-morpholino-3-pyridyl NH n-butyl OCOOEt2-hydroxy-3-pyridyl NH n-butyl OCOOEt 4-hydroxy-3-pyridyl NH n-butylOCOOEt 5-hydroxy-3-pyridyl NH n-butyl OCOOEt 6-hydroxy-3-pyridyl NHn-butyl OCOOEt 2-mercapto-3-pyridyl NH n-butyl OCOOEt4-mercapto-3-pyridyl NH n-butyl OCOOEt 5-mercapto-3-pyridyl NH n-butylOCCOEt 6-mercapto-3-pyridyl NH n-butyl OCOOEt 2-methylthio-3-pyridyl NHn-butyl OCOOEt 4-methylthio-3-pyridyl NH n-butyl OCOOEt5-methylthio-3-pyridyl NH n-butyl OCOOEt 6-methylthio-3-pyridyl NHn-butyl OCOOEt 2,6-dimethyl-3-pyridyl NH n-butyl OCOOEt5,6-dimethyl-3-pyridyl NH n-butyl OCOOEt 2,6-diethyl-3-pyridyl NHn-butyl OCOOEt 5,6-diethyl-3-pyridyl NH n-butyl OCOOEt2,6-dimethoxy-3-pyridyl NH n-butyl OCOOEt 5,6-dimethoxy-3-pyridyl NHn-butyl OCOOEt 2,6-diethoxy-3-pyridyl NH n-butyl OCOOEt5,6-diethoxy-3-pyridyl NH n-butyl OCOOEt 2,6-dichloro-3-pyridyl NHn-butyl OCOOEt 5,6-dichloro-3-pyridyl NH n-butyl OCOOEt5-chloro-6-methoxy-3-pyridyl NH n-butyl OCOOEt5-chloro-6-ethoxy-3-pyridyl NH n-butyl OCOOEt2-chloro-6-methyl-3-pyridyl NH n-butyl OCOOEt6-chloro-2-methyl-3-pyridyl NH n-butyl OCOOEt 2-methyl-4-pyridyl NHn-butyl OCOOEt 2-ethyl-4-pyridyl NH n-butyl OCOOEt 2-methoxy-4-pyridylNH n-butyl OCOOEt 2-ethoxy-4-pyridyl NH n-butyl OCOOEt2-chloro-4-pyridyl NH n-butyl OCOOEt 2-dimethylamino-4-pyridyl NHn-butyl OCOOEt 2-(1-pyrrolidinyl)-4-pyridyl NH n-butyl OCOOEt2-piperidino-4-pyridyl NH n-butyl OCOOEt 2-morpholino-4-pyridyl NHn-butyl OCOOEt 2-methylthio-4-pyridyl NH n-butyl OCOOEt 2-pyrazinyl NHn-butyl OCOOEt 5-methyl-2-pyrazinyl NH n-butyl OCOOEt5-ethyl-2-pyrazinyl NH n-butyl OCOOEt 5-methoxy-2-pyrazinyl NH n-butylOCOOEt 5-ethoxy-2-pyrazinyl NH n-butyl OCOOEt 5-chloro-2-pyrazinyl NHn-butyl OCOOEt 6-methyl-2-pyrazinyl NH n-butyl OCOOEt6-methoxy-2-pyrazinyl NH n-butyl OCOOEt 6-chloro-2-pyrazinyl NH n-pentylOH 2-pyridyl NH n-pentyl OH 3-pyridyl NH n-pentyl OH 4-pyridyl NHn-pentyl OH 2-methyl-3-pyridyl NH n-pentyl OH 4-methyl-3-pyridyl NHn-pentyl OH 5-methyl-3-pyridyl NH n-pentyl OH 6-methyl-3-pyridyl NHn-pentyl OH 2-ethyl-3-pyridyl NH n-pentyl OH 4-ethyl-3-pyridyl NHn-pentyl OH 5-ethyl-3-pyridyl NH n-pentyl OH 6-ethyl-3-pyridyl NHn-pentyl OH 2-methoxy-3-pyridyl NH n-pentyl OH 4-methoxy-3-pyridyl NHn-pentyl OH 5-methoxy-3-pyridyl NH n-pentyl OH 6-methoxy-3-pyridyl NHn-pentyl OH 2-ethoxy-3-pyridyl NH n-pentyl OH 4-ethoxy-3-pyridyl NHn-pentyl OH 5-ethoxy-3-pyridyl NH n-pentyl OH 6-ethoxy-3-pyridyl NHn-pentyl OH 2-chloro-3-pyridyl NH n-pentyl OH 4-chloro-3-pyridyl NHn-pentyl OH 5-chloro-3-pyridyl NH n-pentyl OH 6-chloro-3-pyridyl NHn-pentyl OH 2-fluoro-3-pyridyl NH n-pentyl OH 4-fluoro-3-pyridyl NHn-pentyl OH 5-fluoro-3-pyridyl NH n-pentyl OH 6-fluoro-3-pyridyl NHn-pentyl OH 2-dimethylamino-3-pyridyl NH n-pentyl OH4-dimethylamino-3-pyridyl NH n-pentyl OH 5-dimethylamino-3-pyridyl NHn-pentyl OH 6-dimethylamino-3-pyridyl NH n-pentyl OH2-(1-pyrrolidinyl)-3-pyridyl NH n-pentyl OH 3-(1-pyrrolidinyl)-3-pyridylNH n-pentyl OH 5-(1-pyrrolidinyl)-3-pyridyl NH n-pentyl OH6-(1-pyrrolidinyl)-3-pyridyl NH n-pentyl OH 2-piperidino-3-pyridyl NHn-pentyl OH 4-piperidino-3-pyridyl NH n-pentyl OH 5-piperidino-3-pyridylNH n-pentyl OH 6-piperidino-3-pyridyl NH n-pentyl OH2-morpholino-3-pyridyl NH n-pentyl OH 4-morpholino-3-pyridyl NH n-pentylOH 5-morpholino-3-pyridyl NH n-pentyl OH 6-morpholino-3-pyridyl NHn-pentyl OH 2-hydroxy-3-pyridyl NH n-pentyl OH 4-hydroxy-3-pyridyl NHn-pentyl OH 5-hydroxy-3-pyridyl NH n-pentyl OH 6-hydroxy-3-pyridyl NHn-pentyl OH 2-mercapto-3-pyridyl NH n-pentyl OH 4-mercapto-3-pyridyl NHn-pentyl OH 5-mercapto-3-pyridyl NH n-pentyl OH 6-mercapto-3-pyridyl NHn-pentyl OH 2-methylthio-3-pyridyl NH n-pentyl OH 4-methylthio-3-pyridylNH n-pentyl OH 5-methylthio-3-pyridyl NH n-pentyl OH6-methylthio-3-pyridyl NH n-pentyl OH 2,6-dimethyl-3-pyridyl NH n-pentylOH 5,6-dimethyl-3-pyridyl NH n-pentyl OH 2,6-diethyl-3-pyridyl NHn-pentyl OH 5,6-diethyl-3-pyridyl NH n-pentyl OH 2,6-dimethoxy-3-pyridylNH n-pentyl OH 5,6-dimethoxy-3-pyridyl NH n-pentyl OH2,6-diethoxy-3-pyridyl NH n-pentyl OH 5,6-diethoxy-3-pyridyl NH n-pentylOH 2,6-dichloro-3-pyridyl NH n-pentyl OH 5,6-dichloro-3-pyridyl NHn-pentyl OH 5-chloro-6-methoxy-3-pyridyl NH n-pentyl OH5-chloro-6-ethoxy-3-pyridyl NH n-pentyl OH 2-chloro-6-methyl-3-pyridylNH n-pentyl OH 6-chloro-2-methyl-3-pyridyl NH n-pentyl OH2-methyl-4-pyridyl NH n-pentyl OH 2-ethyl-4-pyridyl NH n-pentyl OH2-methoxy-4-pyridyl NH n-pentyl OH 2-ethoxy-4-pyridyl NH n-pentyl OH2-chloro-4-pyridyl NH n-pentyl OH 2-dimethylamino-4-pyridyl NH n-pentylOH 2-(1-pyrrolidinyl)-4-pyridyl NH n-pentyl OH 2-piperidino-4-pyridyl NHn-pentyl OH 2-morpholino-4-pyridyl NH n-pentyl OH 2-methylthio-4-pyridylNH n-pentyl OH 2-pyrazinyl NH n-pentyl OH 5-methyl-2-pyrazinyl NHn-pentyl OH 5-ethyl-2-pyrazinyl NH n-pentyl OH 5-methoxy-2-pyrazinyl NHn-pentyl OH 5-ethoxy-2-pyrazinyl NH n-pentyl OH 5-chloro-2-pyrazinyl NHn-pentyl OH 6-methyl-2-pyrazinyl NH n-pentyl OH 6-methoxy-2-pyrazinyl NHn-pentyl OH 6-chloro-2-pyrazinyl NH n-pentyl OCOOMe 2-pyridyl NHn-pentyl OCOOMe 3-pyridyl NH n-pentyl OCOOMe 4-pyridyl NH n-pentylOCOOMe 2-methyl-3-pyridyl NH n-pentyl OCOOMe 4-methyl-3-pyridyl NHn-pentyl OCOOMe 5-methyl-3-pyridyl NH n-pentyl OCOOMe 6-methyl-3-pyridylNH n-pentyl OCOOMe 2-ethyl-3-pyridyl NH n-pentyl OCOOMe4-ethyl-3-pyridyl NH n-pentyl OCOOMe 5-ethyl-3-pyridyl NH n-pentylOCOOMe 6-ethyl-3-pyridyl NH n-pentyl OCOOMe 2-methoxy-3-pyridyl NHn-pentyl OCOOMe 4-methoxy-3-pyridyl NH n-pentyl OCOOMe5-methoxy-3-pyridyl NH n-pentyl OCOOMe 6-methoxy-3-pyridyl NH n-pentylOCOOMe 2-ethoxy-3-pyridyl NH n-pentyl OCOOMe 4-ethoxy-3-pyridyl NHn-pentyl OCOOMe 5-ethoxy-3-pyridyl NH n-pentyl OCOOMe 6-ethoxy-3-pyridylNH n-pentyl OCOOMe 2-chloro-3-pyridyl NH n-pentyl OCOOMe4-chloro-3-pyridyl NH n-pentyl OCOOMe 5-chloro-3-pyridyl NH n-pentylOCOOMe 6-chloro-3-pyridyl NH n-pentyl OCOOMe 2-fluoro-3-pyridyl NHn-pentyl OCOOMe 4-fluoro-3-pyridyl NH n-pentyl OCOOMe 5-fluoro-3-pyridylNH n-pentyl OCOOMe 6-fluoro-3-pyridyl NH n-pentyl OCOOMe2-dimethylamino-3-pyridyl NH n-pentyl OCOOMe 4-dimethylamino-3-pyridylNH n-pentyl OCOOMe 5-dimethylamino-3-pyridyl NH n-pentyl OCOOMe6-dimethylamino-3-pyridyl NH n-pentyl OCOOMe2-(1-pyrrolidinyl)-3-pyridyl NH n-pentyl OCOOMe3-(1-pyrrolidinyl)-3-pyridyl NH n-pentyl OCOOMe5-(1-pyrrolidinyl)-3-pyridyl NH n-pentyl OCOOMe6-(1-pyrrolidinyl)-3-pyridyl NH n-pentyl OCOOMe 2-piperidino-3-pyridylNH n-pentyl OCOOMe 4-piperidino-3-pyridyl NH n-pentyl OCOOMe5-piperidino-3-pyridyl NH n-pentyl OCOOMe 6-piperidino-3-pyridyl NHn-pentyl OCOOMe 2-morpholino-3-pyridyl NH n-pentyl OCOOMe4-morpholino-3-pyridyl NH n-pentyl OCOOMe 5-morpholino-3-pyridyl NHn-pentyl OCOOMe 6-morpholino-3-pyridyl NH n-pentyl OCOOMe2-hydroxy-3-pyridyl NH n-pentyl OCOOMe 4-hydroxy-3-pyridyl NH n-pentylOCOOMe 5-hydroxy-3-pyridyl NH n-pentyl OCOOMe 6-hydroxy-3-pyridyl NHn-pentyl OCOOMe 2-mercapto-3-pyridyl NH n-pentyl OCOOMe4-mercapto-3-pyridyl NH n-pentyl OCOOMe 5-mercapto-3-pyridyl NH n-pentylOCOOMe 6-mercapto-3-pyridyl NH n-pentyl OCOOMe 2-methylthio-3-pyridyl NHn-pentyl OCOOMe 4-methylthio-3-pyridyl NH n-pentyl OCOOMe5-methylthio-3-pyridyl NH n-pentyl OCOOMe 6-methylthio-3-pyridyl NHn-pentyl OCOOMe 2,6-dimethyl-3-pyridyl NH n-pentyl OCOOMe5,6-dimethyl-3-pyridyl NH n-pentyl OCOOMe 2,6-diethyl-3-pyridyl NHn-pentyl OCOOMe 5,6-diethyl-3-pyridyl NH n-pentyl OCOOMe2,6-dimethoxy-3-pyridyl NH n-pentyl OCOOMe 5,6-dimethoxy-3-pyridyl NHn-pentyl OCOOMe 2,6-diethoxy-3-pyridyl NH n-pentyl OCOOMe5,6-diethoxy-3-pyridyl NH n-pentyl OCOOMe 2,6-dichloro-3-pyridyl NHn-pentyl OCOOMe 5,6-dichloro-3-pyridyl NH n-pentyl OCOOMe5-chloro-6-methoxy-3-pyridyl NH n-pentyl OCOOMe5-chloro-6-ethoxy-3-pyridyl NH n-pentyl OCOOMe2-chloro-6-methyl-3-pyridyl NH n-pentyl OCOOMe6-chloro-2-methyl-3-pyridyl NH n-pentyl OCOOMe 2-methyl-4-pyridyl NHn-pentyl OCOOMe 2-ethyl-4-pyridyl NH n-pentyl OCOOMe 2-methoxy-4-pyridylNH n-pentyl OCOOMe 2-ethoxy-4-pyridyl NH n-pentyl OCOOMe2-chloro-4-pyridyl NH n-pentyl OCOOMe 2-dimethylamino-4-pyridyl NHn-pentyl OCOOMe 2-(1-pyrrolidinyl)-4-pyridyl NH n-pentyl OCOOMe2-piperidino-4-pyridyl NH n-pentyl OCOOMe 2-morpholino-4-pyridyl NHn-pentyl OCOOMe 2-methylthio-4-pyridyl NH n-pentyl OCOOMe 2-pyrazinyl NHn-pentyl OCOOMe 5-methyl-2-pyrazinyl NH n-pentyl OCOOMe5-ethyl-2-pyrazinyl NH n-pentyl OCOOMe 5-methoxy-2-pyrazinyl NH n-pentylOCOOMe 5-ethoxy-2-pyrazinyl NH n-pentyl OCOOMe 5-chloro-2-pyrazinyl NHn-pentyl OCOOMe 6-methyl-2-pyrazinyl NH n-pentyl OCOOMe6-methoxy-2-pyrazinyl NH n-pentyl OCOOMe 6-chloro-2-pyrazinyl NHn-pentyl OCOOEt 2-pyridyl NH n-pentyl OCOOEt 3-pyridyl NH n-pentylOCOOEt 4-pyridyl NH n-pentyl OCOOEt 2-methyl-3-pyridyl NH n-pentylOCOOEt 4-methyl-3-pyridyl NH n-pentyl OCOOEt 5-methyl-3-pyridyl NHn-pentyl OCOOEt 6-methyl-3-pyridyl NH n-pentyl OCOOEt 2-ethyl-3-pyridylNH n-pentyl OCOOEt 4-ethyl-3-pyridyl NH n-pentyl OCOOEt5-ethyl-3-pyridyl NH n-pentyl OCOOEt 6-ethyl-3-pyridyl NH n-pentylOCOOEt 2-methoxy-3-pyridyl NH n-pentyl OCOOEt 4-methoxy-3-pyridyl NHn-pentyl OCOOEt 5-methoxy-3-pyridyl NH n-pentyl OCOOEt6-methoxy-3-pyridyl NH n-pentyl OCOOEt 2-ethoxy-3-pyridyl NH n-pentylOCOOEt 4-ethoxy-3-pyridyl NH n-pentyl OCOOEt 5-ethoxy-3-pyridyl NHn-pentyl OCOOEt 6-ethoxy-3-pyridyl NH n-pentyl OCOOEt 2-chloro-3-pyridylNH n-pentyl OCOOEt 4-chloro-3-pyridyl NH n-pentyl OCOOEt5-chloro-3-pyridyl NH n-pentyl OCOOEt 6-chloro-3-pyridyl NH n-pentylOCOOEt 2-fluoro-3-pyridyl NH n-pentyl OCOOEt 4-fluoro-3-pyridyl NHn-pentyl OCOOEt 5-fluoro-3-pyridyl NH n-pentyl OCOOEt 6-fluoro-3-pyridylNH n-pentyl OCOOEt 2-dimethylamino-3-pyridyl NH n-pentyl OCOOEt4-dimethylamino-3-pyridyl NH n-pentyl OCOOEt 5-dimethylamino-3-pyridylNH n-pentyl OCOOEt 6-dimethylamino-3-pyridyl NH n-pentyl OCOOEt2-(1-pyrrolidinyl)-3-pyridyl NH n-pentyl OCOOEt3-(1-pyrrolidinyl)-3-pyridyl NH n-pentyl OCOOEt5-(1-pyrrolidinyl)-3-pyridyl NH n-pentyl OCOOEt6-(1-pyrrolidinyl)-3-pyridyl NH n-pentyl OCOOEt 2-piperidino-3-pyridylNH n-pentyl OCOOEt 4-piperidino-3-pyridyl NH n-pentyl OCOOEt5-piperidino-3-pyridyl NH n-pentyl OCOOEt 6-piperidino-3-pyridyl NHn-pentyl OCOOEt 2-morpholino-3-pyridyl NH n-pentyl OCOOEt4-morpholino-3-pyridyl NH n-pentyl OCOOEt 5-morpholino-3-pyridyl NHn-pentyl OCOOEt 6-morpholino-3-pyridyl NH n-pentyl OCOOEt2-hydroxy-3-pyridyl NH n-pentyl OCOOEt 4-hydroxy-3-pyridyl NH n-pentylOCOOEt 5-hydroxy-3-pyridyl NH n-pentyl OCOOEt 6-hydroxy-3-pyridyl NHn-pentyl OCOOEt 2-mercapto-3-pyridyl NH n-pentyl OCOOEt4-mercapto-3-pyridyl NH n-pentyl OCOOEt 5-mercapto-3-pyridyl NH n-pentylOCOOEt 6-mercapto-3-pyridyl NH n-pentyl OCOOEt 2-methylthio-3-pyridyl NHn-pentyl OCOOEt 4-methylthio-3-pyridyl NH n-pentyl OCOOEt5-methylthio-3-pyridyl NH n-pentyl OCOOEt 6-methylthio-3-pyridyl NHn-pentyl OCOOEt 2,6-dimethyl-3-pyridyl NH n-pentyl OCOOEt5,6-dimethyl-3-pyridyl NH n-pentyl OCOOEt 2,6-diethyl-3-pyridyl NHn-pentyl OCOOEt 5,6-diethyl-3-pyridyl NH n-pentyl OCOOEt2,6-dimethoxy-3-pyridyl NH n-pentyl OCOOEt 5,6-dimethoxy-3-pyridyl NHn-pentyl OCOOEt 2,6-diethoxy-3-pyridyl NH n-pentyl OCOOEt5,6-diethoxy-3-pyridyl NH n-pentyl OCOOEt 2,6-dichloro-3-pyridyl NHn-pentyl OCOOEt 5,6-dichloro-3-pyridyl NH n-pentyl OCOOEt5-chloro-6-methoxy-3-pyridyl NH n-pentyl OCOOEt5-chloro-6-ethoxy-3-pyridyl NH n-pentyl OCOOEt2-chloro-6-methyl-3-pyridyl NH n-pentyl OCOOEt6-chloro-2-methyl-3-pyridyl NH n-pentyl OCOOEt 2-methyl-4-pyridyl NHn-pentyl OCOOEt 2-ethyl-4-pyridyl NH n-pentyl OCOOEt 2-methoxy-4-pyridylNH n-pentyl OCOOEt 2-ethoxy-4-pyridyl NH n-pentyl OCOOEt2-chloro-4-pyridyl NH n-pentyl OCOOEt 2-dimethylamino-4-pyridyl NHn-pentyl OCOOEt 2-(1-pyrrolidinyl)-4-pyridyl NH n-pentyl OCOOEt2-piperidino-4-pyridyl NH n-pentyl OCOOEt 2-morpholino-4-pyridyl NHn-pentyl OCOOEt 2-methylthio-4-pyridyl NH n-pentyl OCOOEt 2-pyrazinyl NHn-pentyl OCOOEt 5-methyl-2-pyrazinyl NH n-pentyl OCOOEt5-ethyl-2-pyrazinyl NH n-pentyl OCOOEt 5-methoxy-2-pyrazinyl NH n-pentylOCOOEt 5-ethoxy-2-pyrazinyl NH n-pentyl OCOOEt 5-chloro-2-pyrazinyl NHn-pentyl OCOOEt 6-methyl-2-pyrazinyl NH n-pentyl OCOOEt6-methoxy-2-pyrazinyl NH n-pentyl OCOOEt 6-chloro-2-pyrazinyl O propylOH 2-pyridyl O propyl OH 3-pyridyl O propyl OH 4-pyridyl O propyl OH2-methyl-3-pyridyl O propyl OH 4-methyl-3-pyridyl O propyl OH5-methyl-3-pyridyl O propyl OH 6-methyl-3-pyridyl O propyl OH2-ethyl-3-pyridyl O propyl OH 4-ethyl-3-pyridyl O propyl OH5-ethyl-3-pyridyl O propyl OH 6-ethyl-3-pyridyl O propyl OH2-methoxy-3-pyridyl O propyl OH 4-methoxy-3-pyridyl O propyl OH5-methoxy-3-pyridyl O propyl OH 6-methoxy-3-pyridyl O propyl OH2-ethoxy-3-pyridyl O propyl OH 4-ethoxy-3-pyridyl O propyl OH5-ethoxy-3-pyridyl O propyl OH 6-ethoxy-3-pyridyl O propyl OH2-chloro-3-pyridyl O propyl OH 4-chloro-3-pyridyl O propyl OH5-chloro-3-pyridyl O propyl OH 6-chloro-3-pyridyl O propyl OH2-fluoro-3-pyridyl O propyl OH 4-fluoro-3-pyridyl O propyl OH5-fluoro-3-pyridyl O propyl OH 6-fluoro-3-pyridyl O propyl OH2-dimethylamino-3-pyridyl O propyl OH 4-dimethylamino-3-pyridyl O propylOH 5-dimethylamino-3-pyridyl O propyl OH 6-dimethylamino-3-pyridyl Opropyl OH 2-(1-pyrrolidinyl)-3-pyridyl O propyl OH3-(1-pyrrolidinyl)-3-pyridyl O propyl OH 5-(1-pyrrolidinyl)-3-pyridyl Opropyl OH 6-(1-pyrrolidinyl)-3-pyridyl O propyl OH2-piperidino-3-pyridyl O propyl OH 4-piperidino-3-pyridyl O propyl OH5-piperidino-3-pyridyl O propyl OH 6-piperidino-3-pyridyl O propyl OH2-morpholino-3-pyridyl O propyl OH 4-morpholino-3-pyridyl O propyl OH5-morpholino-3-pyridyl O propyl OH 6-morpholino-3-pyridyl O propyl OH2-hydroxy-3-pyridyl O propyl OH 4-hydroxy-3-pyridyl O propyl OH5-hydroxy-3-pyridyl O propyl OH 6-hydroxy-3-pyridyl O propyl OH2-mercapto-3-pyridyl O propyl OH 4-mercapto-3-pyridyl O propyl OH5-mercapto-3-pyridyl O propyl OH 6-mercapto-3-pyridyl O propyl OH2-methylthio-3-pyridyl O propyl OH 4-methylthio-3-pyridyl O propyl OH5-methylthio-3-pyridyl O propyl OH 6-methylthio-3-pyridyl O propyl OH2,6-dimethyl-3-pyridyl O propyl OH 5,6-dimethyl-3-pyridyl O propyl OH2,6-diethyl-3-pyridyl O propyl OH 5,6-diethyl-3-pyridyl O propyl OH2,6-dimethoxy-3-pyridyl O propyl OH 5,6-dimethoxy-3-pyridyl O propyl OH2,6-diethoxy-3-pyridyl O propyl OH 5,6-diethoxy-3-pyridyl O propyl OH2,6-dichloro-3-pyridyl O propyl OH 5,6-dichloro-3-pyridyl O propyl OH5-chloro-6-methoxy-3-pyridyl O propyl OH 5-chloro-6-ethoxy-3-pyridyl Opropyl OH 2-chloro-6-methyl-3-pyridyl O propyl OH6-chloro-2-methyl-3-pyridyl O propyl OH 2-methyl-4-pyridyl O propyl OH2-ethyl-4-pyridyl O propyl OH 2-methoxy-4-pyridyl O propyl OH2-ethoxy-4-pyridyl O propyl OH 2-chloro-4-pyridyl O propyl OH2-dimethylamino-4-pyridyl O propyl OH 2-(1-pyrrolidinyl)-4-pyridyl Opropyl OH 2-piperidino-4-pyridyl O propyl OH 2-morpholino-4-pyridyl Opropyl OH 2-methylthio-4-pyridyl O propyl OH 2-pyrazinyl O propyl OH5-methyl-2-pyrazinyl O propyl OH 5-ethyl-2-pyrazinyl O propyl OH5-methoxy-2-pyrazinyl O propyl OH 5-ethoxy-2-pyrazinyl O propyl OH5-chloro-2-pyrazinyl O propyl OH 6-methyl-2-pyrazinyl O propyl OH6-methoxy-2-pyrazinyl O propyl OH 6-chloro-2-pyrazinyl O propyl OCOOMe2-pyridyl O propyl OCOOMe 3-pyridyl O propyl OCOOMe 4-pyridyl O propylOCOOMe 2-methyl-3-pyridyl O propyl OCOOMe 4-methyl-3-pyridyl O propylOCOOMe 5-methyl-3-pyridyl O propyl OCOOMe 6-methyl-3-pyridyl O propylOCOOMe 2-ethyl-3-pyridyl O propyl OCOOMe 4-ethyl-3-pyridyl O propylOCOOMe 5-ethyl-3-pyridyl O propyl OCOOMe 6-ethyl-3-pyridyl O propylOCOOMe 2-methoxy-3-pyridyl O propyl OCOOMe 4-methoxy-3-pyridyl O propylOCOOMe 5-methoxy-3-pyridyl O propyl OCOOMe 6-methoxy-3-pyridyl O propylOCOOMe 2-ethoxy-3-pyridyl O propyl OCOOMe 4-ethoxy-3-pyridyl O propylOCOOMe 5-ethoxy-3-pyridyl O propyl OCOOMe 6-ethoxy-3-pyridyl O propylOCOOMe 2-chloro-3-pyridyl O propyl OCOOMe 4-chloro-3-pyridyl O propylOCOOMe 5-chloro-3-pyridyl O propyl OCOOMe 6-chloro-3-pyridyl O propylOCOOMe 2-fluoro-3-pyridyl O propyl OCOOMe 4-fluoro-3-pyridyl O propylOCOOMe 5-fluoro-3-pyridyl O propyl OCOOMe 6-fluoro-3-pyridyl O propylOCOOMe 2-dimethylamino-3-pyridyl O propyl OCOOMe4-dimethylamino-3-pyridyl O propyl OCOOMe 5-dimethylamino-3-pyridyl Opropyl OCOOMe 6-dimethylamino-3-pyridyl O propyl OCOOMe2-(1-pyrrolidinyl)-3-pyridyl O propyl OCOOMe3-(1-pyrrolidinyl)-3-pyridyl O propyl OCOOMe5-(1-pyrrolidinyl)-3-pyridyl O propyl OCOOMe6-(1-pyrrolidinyl)-3-pyridyl O propyl OCOOMe 2-piperidino-3-pyridyl Opropyl OCOOMe 4-piperidino-3-pyridyl O propyl OCOOMe5-piperidino-3-pyridyl O propyl OCOOMe 6-piperidino-3-pyridyl O propylOCOOMe 2-morpholino-3-pyridyl O propyl OCOOMe 4-morpholino-3-pyridyl Opropyl OCOOMe 5-morpholino-3-pyridyl O propyl OCOOMe6-morpholino-3-pyridyl O propyl OCOOMe 2-hydroxy-3-pyridyl O propylOCOOMe 4-hydroxy-3-pyridyl O propyl OCOOMe 5-hydroxy-3-pyridyl O propylOCOOMe 6-hydroxy-3-pyridyl O propyl OCOOMe 2-mercapto-3-pyridyl O propylOCOOMe 4-mercapto-3-pyridyl O propyl OCOOMe 5-mercapto-3-pyridyl Opropyl OCOOMe 6-mercapto-3-pyridyl O propyl OCOOMe2-methylthio-3-pyridyl O propyl OCOOMe 4-methylthio-3-pyridyl O propylOCOOMe 5-methylthio-3-pyridyl O propyl OCOOMe 6-methylthio-3-pyridyl Opropyl OCOOMe 2,6-dimethyl-3-pyridyl O propyl OCOOMe5,6-dimethyl-3-pyridyl O propyl OCOOMe 2,6-diethyl-3-pyridyl O propylOCOOMe 5,6-diethyl-3-pyridyl O propyl OCOOMe 2,6-dimethoxy-3-pyridyl Opropyl OCOOMe 5,6-dimethoxy-3-pyridyl O propyl OCOOMe2,6-diethoxy-3-pyridyl O propyl OCOOMe 5,6-diethoxy-3-pyridyl O propylOCOOMe 2,6-dichloro-3-pyridyl O propyl OCOOMe 5,6-dichloro-3-pyridyl Opropyl OCOOMe 5-chloro-6-methoxy-3-pyridyl O propyl OCOOMe5-chloro-6-ethoxy-3-pyridyl O propyl OCOOMe 2-chloro-6-methyl-3-pyridylO propyl OCOOMe 6-chloro-2-methyl-3-pyridyl O propyl OCOOMe2-methyl-4-pyridyl O propyl OCOOMe 2-ethyl-4-pyridyl O propyl OCOOMe2-methoxy-4-pyridyl O propyl OCOOMe 2-ethoxy-4-pyridyl O propyl OCOOMe2-chloro-4-pyridyl O propyl OCOOMe 2-dimethylamino-4-pyridyl O propylOCOOMe 2-(1-pyrrolidinyl)-4-pyridyl O propyl OCOOMe2-piperidino-4-pyridyl O propyl OCOOMe 2-morpholino-4-pyridyl O propylOCOOMe 2-methylthio-4-pyridyl O propyl OCOOMe 2-pyrazinyl O propylOCOOMe 5-methyl-2-pyrazinyl O propyl OCOOMe 5-ethyl-2-pyrazinyl O propylOCOOMe 5-methoxy-2-pyrazinyl O propyl OCOOMe 5-ethoxy-2-pyrazinyl Opropyl OCOOMe 5-chloro-2-pyrazinyl O propyl OCOOMe 6-methyl-2-pyrazinylO propyl OCOOMe 6-methoxy-2-pyrazinyl O propyl OCOOMe6-chloro-2-pyrazinyl O propyl OCOOEt 2-pyridyl O propyl OCOOEt 3-pyridylO propyl OCOOEt 4-pyridyl O propyl OCOOEt 2-methyl-3-pyridyl O propylOCOOEt 4-methyl-3-pyridyl O propyl OCOOEt 5-methyl-3-pyridyl O propylOCOOEt 6-methyl-3-pyridyl O propyl OCOOEt 2-ethyl-3-pyridyl O propylOCOOEt 4-ethyl-3-pyridyl O propyl OCOOEt 5-ethyl-3-pyridyl O propylOCOOEt 6-ethyl-3-pyridyl O propyl OCOOEt 2-methoxy-3-pyridyl O propylOCOOEt 4-methoxy-3-pyridyl O propyl OCOOEt 5-methoxy-3-pyridyl O propylOCOOEt 6-methoxy-3-pyridyl O propyl OCOOEt 2-ethoxy-3-pyridyl O propylOCOOEt 4-ethoxy-3-pyridyl O propyl OCOOEt 5-ethoxy-3-pyridyl O propylOCOOEt 6-ethoxy-3-pyridyl O propyl OCOOEt 2-chloro-3-pyridyl O propylOCOOEt 4-chloro-3-pyridyl O propyl OCOOEt 5-chloro-3-pyridyl O propylOCOOEt 6-chloro-3-pyridyl O propyl OCOOEt 2-fluoro-3-pyridyl O propylOCOOEt 4-fluoro-3-pyridyl O propyl OCOOEt 5-fluoro-3-pyridyl O propylOCOOEt 6-fluoro-3-pyridyl O propyl OCOOEt 2-dimethylamino-3-pyridyl Opropyl OCOOEt 4-dimethylamino-3-pyridyl O propyl OCOOEt6-dimethylamino-3-pyridyl O propyl OCOOEt 6-dimethylamino-3-pyridyl Opropyl OCOOEt 2-(1-pyrrolidinyl)-3-pyridyl O propyl OCOOEt3-(1-pyrrolidinyl)-3-pyridyl O propyl OCOOEt5-(1-pyrrolidinyl)-3-pyridyl O propyl OCOOEt6-(1-pyrrolidinyl)-3-pyridyl O propyl OCOOEt 2-piperidino-3-pyridyl Opropyl OCOOEt 4-piperidino-3-pyridyl O propyl OCOCEt5-piperidino-3-pyridyl O propyl OCOOEt 6-piperidino-3-pyridyl O propylOCOOEt 2-morpholino-3-pyridyl O propyl OCOOEt 4-morpholino-3-pyridyl Opropyl OCOOEt 5-morpholino-3-pyridyl O propyl OCOOEt6-morpholino-3-pyridyl O propyl OCOOEt 2-hydroxy-3-pyridyl O propylOCOOEt 4-hydroxy-3-pyridyl O propyl OCOOEt 5-hydroxy-3-pyridyl O propylOCOOEt 6-hydroxy-3-pyridyl O propyl OCOOEt 2-mercapto-3-pyridyl O propylOCOOEt 4-mercapto-3-pyridyl O propyl OCOOEt 5-mercapto-3-pyridyl Opropyl OCOOEt 6-mercapto-3-pyridyl O propyl OCOOEt2-methylthio-3-pyridyl O propyl OCOOEt 4-methylthio-3-pyridyl O propylOCOOEt 5-methylthio-3-pyridyl O propyl OOOOEt 5-methylthio-3-pyridyl Opropyl OCOOEt 2,6-dimethyl-3-pyridyl O propyl OCOOEt5,6-dimethyl-3-pyridyl O propyl OCOOEt 2,6-diethyl-3-pyridyl O propylOCOOEt 5,6-diethyl-3-pyridyl O propyl OCOOEt 2,6-dimethoxy-3-pyridyl Opropyl OCOOEt 5,6-dimethoxy-3-pyridyl O propyl OCOOEt2,6-diethoxy-3-pyridyl O propyl OCOOEt 5,6-diethoxy-3-pyridyl O propylOCOOEt 2,6-dichloro-3-pyridyl O propyl OCOOEt 5,6-dichloro-3-pyridyl Opropyl OCOOEt 5-chloro-6-methoxy-3-pyridyl O propyl OCOOEt5-chloro-6-ethoxy-3-pyridyl O propyl OCOOEt 2-chloro-6-methyl-3-pyridylO propyl OCOOEt 6-chloro-2-methyl-3-pyridyl O propyl OCOOEt2-methyl-4-pyridyl O propyl OCOOEt 2-ethyl-4-pyridyl O propyl OCOOEt2-methoxy-4-pyridyl O propyl OCOOEt 2-ethoxy-4-pyridyl O propyl OCOOEt2-chloro-4-pyridyl O propyl OCOOEt 2-dimethylamino-4-pyridyl O propylOCOOEt 2-(1-pyrrolidinyl)-4-pyridyl O propyl OCOOEt2-piperidino-4-pyridyl O propyl OCOOEt 2-morpholino-4-pyridyl O propylOCOOEt 2-methylthio-4-pyridyl O propyl OCOOEt 2-pyrazinyl O propylOCOOEt 5-methyl-2-pyrazinyl O propyl OCOOEt 5-ethyl-2-pyrazinyl O propylOCOOEt 5-methoxy-2-pyrazinyl O propyl OCOOEt 5-ethoxy-2-pyrazinyl Opropyl OCOOEt 5-chloro-2-pyrazinyl O propyl OCOOEt 6-methyl-2-pyrazinylO propyl OCOOEt 6-methoxy-2-pyrazinyl O propyl OCOOEt6-chloro-2-pyrazinyl O n-butyl OH 2-pyridyl O n-butyl OH 3-pyridyl On-butyl OH 4-pyridyl O n-butyl OH 2-methyl-3-pyridyl O n-butyl OH4-methyl-3-pyridyl O n-butyl OH 5-methyl-3-pyridyl O n-hntyl OH6-methyl-3-pyridyl O n-butyl OH 2-ethyl-3-pyridyl O n-butyl OH4-ethyl-3-pyridyl O n-butyl OH 5-ethyl-3-pyridyl O n-butyl OH6-ethyl-3-pyridyl O n-butyl OH 2-methoxy-3-pyridyl O n-butyl OH4-methoxy-3-pyridyl O n-butyl OH 5-methoxy-3-pyridyl O n-butyl OH6-methoxy-3-pyridyl O n-butyl OH 2-ethoxy-3-pyridyl O n-butyl OH4-ethoxy-3-pyridyl O n-butyl OH 5-ethoxy-3-pyridyl O n-butyl OH6-ethoxy-3-pyridyl O n-butyl OH 2-chloro-3-pyridyl O n-butyl OH4-chloro-3-pyridyl O n-butyl OH 5-chloro-3-pyridyl O n-butyl OH6-chloro-3-pyridyl O n-butyl OH 2-flouro-3-pyridyl O n-butyl OH4-flouro-3-pyridyl O n-butyl OH 5-flouro-3-pyridyl O n-butyl OH6-fluoro-3-pyridyl O n-butyl OH 2-dimethylamino-3-pyridyl O n-butyl OH4-dimethylamino-3-pyridyl O n-butyl OH 5-dimethylamino-3-pyridyl On-butyl OH 6-dimethylamino-3-pyridyl O n-butyl OH2-(1-pyrrolidinyl)-3-pyridyl O n-butyl OH 3-(1-pyrrolidinyl)-3-pyridyl On-butyl OH 5-(1-pyrrolidinyl)-3-pyridyl O n-butyl OH6-(1-pyrrolidinyl)-3-pyridyl O n-butyl OH 2-piperidino-3-pyridyl On-butyl OH 4-piperidino-3-pyridyl O n-butyl OH 5-piperidino-3-pyridyl On-butyl OH 6-piperidino-3-pyridyl O n-butyl OH 2-morpholino-3-pyridyl On-butyl OH 4-morpholino-3-pyridyl O n-butyl OH 5-morpholino-3-pyridyl On-butyl OH 6-morpholino-3-pyridyl O n-butyl OH 2-hydroxy-3-pyridyl On-butyl OH 4-hydroxy-3-pyridyl O n-butyl OH 5-hydroxy-3-pyridyl On-butyl OH 6-hydroxy-3-pyridyl O n-butyl OH 2-mercapto-3-pyridyl On-butyl OH 4-mercapto-3-pyridyl O n-butyl OH 5-mercapto-3-pyridyl On-butyl OH 6-mercapto-3-pyridyl O n-butyl OH 2-methylthio-3-pyridyl On-butyl OH 4-methylthio-3-pyridyl O n-butyl OH 5-methylthio-3-pyridyl On-butyl OH 6-methylthio-3-pyridyl O n-butyl OH 2,6-dimethyl-3-pyridyl On-butyl OH 5,6-dimethyl-3-pyridyl O n-butyl OH 2,6-diethyl-3-pyridyl On-butyl OH 5,6-diethyl-3-pyridyl O n-butyl OH 2,6-dimethoxy-3-pyridyl On-butyl OH 5,6-dimethoxy-3-pyridyl O n-butyl OH 2,6-diethoxy-3-pyridyl On-butyl OH 5,6-diethoxy-3-pyridyl O n-butyl OH 2,6-dichloro-3-pyridyl On-butyl OH 5,6-dichloro-3-pyridyl O n-butyl OH5-chloro-6-methoxy-3-pyridyl O n-butyl OH 5-chloro-6-ethoxy-3-pyridyl On-butyl OH 2-chloro-6-methyl-3-pyridyl O n-butyl OH6-chloro-2-methyl-3-pyridyl O n-butyl OH 2-methyl-4-pyridyl O n-butyl OH2-ethyl-4-pyridyl O n-butyl OH 2-methoxy-4-pyridyl O n-butyl OH2-ethoxy-4-pyridyl O n-butyl OH 2-chloro-4-pyridyl O n-butyl OH2-dimethylamino-4-pyridyl O n-butyl OH 2-(1-pyrrolidiny1)-4-pyridyl On-butyl OH 2-piperidino-4-pyridyl O n-butyl OH 2-morpholino-4-pyridyl On-butyl OH 2-methylthio-4-pyridyl O n-butyl OH 2-pyrazinyl O n-butyl OH5-methyl-2-pyrazinyl O n-butyl OH 5-ethyl-2-pyrazinyl O n-butyl OH5-methoxy-2-pyrazinyl O n-butyl OH 5-ethoxy-2-pyrazinyl O n-butyl OH5-chloro-2-pyrazinyl O n-butyl OH 6-methyl-2-pyrazinyl O n-butyl OH6-methoxy-2-pyrazinyl O n-butyl OH 6-chloro-2-pyrazinyl O n-butyl OCOOMe2-pyridyl O n-butyl OCOOMe 3-pyridyl O n-butyl OCOOMe 4-pyridyl On-butyl OCOOMe 2-methyl-3-pyridyl O n-butyl OCOOMe 4-methyl-3-pyridyl On-butyl OCOOMe 5-methyl-3-pyridyl O n-butyl OCOOMe 6-methyl-3-pyridyl On-butyl OCOOMe 2-ethyl-3-pyridyl O n-butyl OCOOMe 4-ethyl-3-pyridyl On-butyl OCOOMe 5-ethyl-3-pyridyl O n-butyl OCOOMe 6-ethyl-3-pyridyl On-butyl OCOOMe 2-methoxy-3-pyridyl O n-butyl OCOOMe 4-methoxy-3-pyridylO n-butyl OCOOMe 5-methoxy-3-pyridyl O n-butyl OCOOMe6-methoxy-3-pyridyl O n-butyl OCOOMe 2-ethoxy-3-pyridyl O n-butyl OCOOMe4-ethoxy-3-pyridyl O n-butyl OCOOMe 5-ethoxy-3-pyridyl O n-butyl OCOOMe6-ethoxy-3-pyridyl O n-butyl OCOOMe 2-chloro-3-pyridyl O n-butyl OCOOMe4-chloro-3-pyridyl O n-butyl OCOOMe 5-chloro-3-pyridyl O n-butyl OCOOMe6-chloro-3-pyridyl O n-butyl OCOOMe 2-fluoro-3-pyridyl O n-butyl OCOOMe4-fluoro-3-pyridyl O n-butyl OCOOMe 5-fluoro-3-pyridyl O n-butyl OCOOMe6-fluoro-3-pyridyl O n-butyl OCOOMe 2-dimethylamino-3-pyridyl O n-butylOCOOMe 4-dimethylamino-3-pyridyl O n-butyl OCOOMe5-dimethylamino-3-pyridyl O n-butyl OCOOMe 6-dimethylamino-3-pyridyl On-butyl OCOOMe 2-(1-pyrrolidinyl)-3-pyridyl O n-butyl OCOOMe3-(1-pyrrolidinyl)-3-pyridyl O n-butyl OCOOMe5-(1-pyrrolidinyl)-3-pyridyl O n-butyl OCOOMe6-(1-pyrrolidinyl)-3-pyridyl O n-butyl OCOOMe 2-piperidino-3-pyridyl On-butyl OCOOMe 4-piperidino-3-pyridyl O n-butyl OCOOMe5-piperidino-3-pyridyl O n-butyl OCOOMe 6-piperidino-3-pyridyl O n-butylOCOOMe 2-morpholino-3-pyridyl O n-butyl OCOOMe 4-morpholino-3-pyridyl On-butyl OCOOMe 5-morpholino-3-pyridyl O n-butyl OCOOMe6-morpholino-3-pyridyl O n-butyl OCOOMe 2-hydroxy-3-pyridyl O n-butylOCOOMe 4-hydroxy-3-pyridyl O n-butyl OCOOMe 5-hydroxy-3-pyridyl On-butyl OCOOMe 6-hydroxy-3-pyridyl O n-butyl OCOOMe 2-mercapto-3-pyridylO n-butyl OCOOMe 4-mercapto-3-pyridyl O n-butyl OCOOMe5-mercapto-3-pyridyl O n-butyl OCOOMe 6-mercapto-3-pyridyl O n-butylOCOOMe 2-methylthio-3-pyridyl O n-butyl OCOOMe 4-methylthio-3-pyridyl On-butyl OCOOMe 5-methylthio-3-pyridyl O n-butyl OCOOMe6-methylthio-3-pyridyl O n-butyl OCOOMe 2,6-dimethyl-3-pyridyl O n-butylOCOOMe 5,6-dimethyl-3-pyridyl O n-butyl OCOOMe 2,6-diethyl-3-pyridyl On-butyl OCOOMe 5,6-diethyl-3-pyridyl O n-butyl OCOOMe2,6-dimethoxy-3-pyridyl O n-butyl OCOOMe 5,6-dimethoxy-3-pyridyl On-butyl OCOOMe 2,6-diethoxy-3-pyridyl O n-butyl OCOOMe5,6-diethoxy-3-pyridyl O n-butyl OCOOMe 2,6-dichloro-3-pyridyl O n-butylOCOOMe 5,6-dichloro-3-pyridyl O n-butyl OCOOMe5-chloro-6-methoxy-3-pyridyl O n-butyl OCOOMe5-chloro-6-ethoxy-3-pyridyl O n-butyl OCOOMe 2-chloro-6-methyl-3-pyridylO n-butyl OCOOMe 6-chloro-2-methyl-3-pyridyl O n-butyl OCOOMe2-methyl-4-pyridyl O n-butyl OCOOMe 2-ethyl-4-pyridyl O n-butyl OCOOMe2-methoxy-4-pyridyl O n-butyl OCOOMe 2-ethoxy-4-pyridyl O n-butyl OCOOMe2-chloro-4-pyridyl O n-butyl OCOOMe 2-dimethylamino-4-pyridyl O n-bvtylOCOOMe 2-(1-pyrrolidinyl)-4-pyridyl O n-butyl OCOOMe2-piperidino-4-pyridyl O n-butyl OCOOMe 2-morpholino-4-pyridyl O n-butylOCOOMe 2-methylthio-4-pyridyl O n-butyl OCOOMe 2-pyrazinyl O n-butylOCOOMe 5-methyl-2-pyrazinyl O n-butyl OCOOMe 5-ethyl-2-pyrazinyl On-butyl OCOOMe 5-methoxy-2-pyrazinyl O n-butyl OCOOMe5-ethoxy-2-pyrazinyl O n-butyl OCOOMe 5-chloro-2-pyrazinyl O n-butylOCOOMe 6-methyl-2-pyrazinyl O n-butyl OCOOMe 6-methoxy-2-pyrazinyl On-butyl OCOOMe 6-chloro-2-pyrazinyl O n-butyl OCOOEt 2-pyridyl O n-butylOCOOEt 3-pyridyl O n-butyl OCOOEt 4-pyridyl O n-butyl OCOOEt2-methyl-3-pyridyl O n-butyl OCOOEt 4-methyl-3-pyridyl O n-butyl OCOOEt5-methyl-3-pyridyl O n-butyl OCOOEt 6-methyl-3-pyridyl O n-butyl OCOOEt2-ethyl-3-pyridyl O n-butyl OCOOEt 4-ethyl-3-pyridyl O n-butyl OCOOEt5-ethyl-3-pyridyl O n-butyl OCOOEt 6-ethyl-3-pyridyl O n-butyl OCOOEt2-methoxy-3-pyridyl O n-butyl OCOOEt 4-methoxy-3-pyridyl O n-butylOCOOEt 5-methoxy-3-pyridyl O n-butyl OCOOEt 6-methoxy-3-pyridyl On-butyl OCOOEt 2-ethoxy-3-pyridyl O n-butyl OCOOEt 4-ethoxy-3-pyridyl On-butyl OCOOEt 5-ethoxy-3-pyridyl O n-butyl OCOOEt 6-ethoxy-3-pyridyl On-butyl OCOOEt 2-chloro-3-pyridyl O n-butyl OCOOEt 4-chloro-3-pyridyl On-butyl OCOOEt 5-chloro-3-pyridyl O n-butyl OCOOEt 6-chloro-3-pyridyl On-butyl OCOOEt 2-fluoro-3-pyridyl O n-butyl OCOOEt 4-fluoro-3-pyridyl On-butyl OCOOEt 5-fluoro-3-pyridyl O n-butyl OCOOEt 6-fluoro-3-pyridyl On-butyl OCOOEt 2-dimethylamino-3-pyridyl O n-butyl OCOOEt4-dimethylamino-3-pyridyl O n-butyl OCOOEt 5-dimethylamino-3-pyridyl On-butyl OCOOEt 6-dimethylamino-3-pyridyl O n-butyl OCOOEt2-(1-pyrrolidinyl)-3-pyridyl O n-butyl OCOOEt3-(1-pyrrolidinyl)-3-pyridyl O n-butyl OCOOEt5-(1-pyrrolidinyl)-3-pyridyl O n-butyl OCOOEt6-(1-pyrrolidinyl)-3-pyridyl O n-butyl OCOOEt 2-piperidino-3-pyridyl On-butyl OCOOEt 4-piperidino-3-pyridyl O n-butyl OCOOEt5-piperidino-3-pyridyl O n-butyl OCOOEt 6-piperidino-3-pyridyl O n-butylOCOOEt 2-morpholino-3-pyridyl O n-butyl OCOOEt 4-morpholino-3-pyridyl On-butyl OCOOEt 5-morpholino-3-pyridyl O n-butyl OCOOEt6-morpholino-3-pyridyl O n-butyl OCOOEt 2-hydroxy-3-pyridyl O n-butylOCOOEt 4-hydroxy-3-pyridyl O n-butyl OCOOEt 5-hydroxy-3-pyridyl On-butyl OCOOEt 6-hydroxy-3-pyridyl O n-butyl OCOOEt 2-mercapto-3-pyridylO n-butyl OCOOEt 4-mercapto-3-pyridyl O n-butyl OCOOEt5-mercapto-3-pyridyl O n-butyl OCOOEt 6-mercapto-3-pyridyl O n-butylOCOOEt 2-methylthio-3-pyridyl O n-butyl OCOOEt 4-methylthio-3-pyridyl On-butyl OCOOEt 5-methylthio-3-pyridyl O n-butyl OCOOEt6-methylthio-3-pyridyl O n-butyl OCOOEt 2,6-dimethyl-3-pyridyl O n-butylOCOOEt 5,6-dimethyl-3-pyridyl O n-butyl OCOOEt 2,6-diethyl-3-pyridyl On-butyl OCOOEt 5,6-diethyl-3-pyridyl O n-butyl OCOOEt2,6-dimethoxy-3-pyridyl O n-butyl OCOOEt 5,6-dimethoxy-3-pyridyl On-butyl OCOOEt 2,6-diethoxy-3-pyridyl O n-butyl OCOOEt5,6-diethoxy-3-pyridyl O n-butyl OCOOEt 2,6-dichloro-3-pyridyl O n-butylOCOOEt 5,6-dichloro-3-pyridyl O n-butyl OCOOEt5-chloro-6-methoxy-3-pyridyl O n-butyl OCOOEt5-chloro-6-ethoxy-3-pyridyl O n-butyl OCOOEt 2-chloro-6-methyl-3-pyridylO n-butyl OCOOEt 6-chloro-2-methyl-3-pyridyl O n-butyl OCOOEt2-methyl-4-pyridyl O n-butyl OCOOEt 2-ethyl-4-pyridyl O n-butyl OCOOEt2-methoxy-4-pyridyl O n-butyl OCOOEt 2-ethoxy-4-pyridyl O n-butyl OCOOEt2-chloro-4-pyridyl O n-butyl OCOOEt 2-dimethylamino-4-pyridyl O n-butylOCOOEt 2-(1-pyrrolidinyl)-4-pyridyl O n-butyl OCOOEt2-piperidino-4-pyridyl O n-butyl OCOOEt 2-morpholino-4-pyridyl O n-butylOCOOEt 2-methylthio-4-pyridyl O n-butyl OCOOEt 2-pyrazinyl O n-butylOCOOEt 5-methyl-2-pyrazinyl O n-butyl OCOOEt 5-ethyl-2-pyrazinyl On-butyl OCOOEt 5-methoxy-2-pyrazinyl O n-butyl OCOOEt5-ethoxy-2-pyrazinyl O n-butyl OCOOEt 5-chloro-2-pyrazinyl O n-butylOCOOEt 6-methyl-2-pyrazinyl O n-butyl OCOOEt 6-methoxy-2-pyrazinyl On-butyl OCOOEt 6-chloro-2-pyrazinyl O n-pentyl OH 2-pyridyl O n-pentylOH 3-pyridyl O n-pentyl OH 4-pyridyl O n-pentyl OH 2-methyl-3-pyridyl On-pentyl OH 4-methyl-3-pyridyl O n-pentyl OH 5-methyl-3-pyridyl On-pentyl OH 6-methyl-3-pyridyl O n-pentyl OH 2-ethyl-3-pyridyl On-pentyl OH 4-ethyl-3-pyridyl O n-pentyl OH 5-ethyl-3-pyridyl O n-pentylOH 6-ethyl-3-pyridyl O n-pentyl OH 2-methoxy-3-pyridyl O n-pentyl OH4-methoxy-3-pyridyl O n-pentyl OH 5-methoxy-3-pyridyl O n-pentyl OH6-methoxy-3-pyridyl O n-pentyl OH 2-ethoxy-3-pyridyl O n-pentyl OH4-ethoxy-3-pyridyl O n-pentyl OH 5-ethoxy-3-pyridyl O n-pentyl OH6-ethoxy-3-pyridyl O n-pentyl OH 2-chloro-3-pyridyl O n-pentyl OH4-chloro-3-pyridyl O n-pentyl OH 5-chloro-3-pyridyl O n-pentyl OH6-chloro-3-pyridyl O n-pentyl OH 2-fluoro-3-pyridyl O n-pentyl OH4-fluoro-3-pyridyl O n-pentyl OH 5-fluoro-3-pyridyl O n-pentyl OH6-fluoro-3-pyridyl O n-pentyl OH 2-dimethylamino-3-pyridyl O n-pentyl OH4-dimethylamino-3-pyridyl O n-pentyl OH 5-dimethylamino-3-pyridyl On-pentyl OH 6-dimethylamino- 3-pyridyl O n-pentyl OH2-(1-pyrrolidinyl)-3-pyridyl O n-pentyl OH 3-(1-pyrrolidinyl)-3-pyridylO n-pentyl OH 5-(1-pyrrolidinyl)-3-pyridyl O n-pentyl OH6-(1-pyrrolidinyl)-3-pyridyl O n-pentyl OH 2-piperidino-3-pyridyl On-pentyl OH 4-piperidino-3-pyridyl O n-pentyl OH 5-piperidino-3-pyridylO n-pentyl OH 6-piperidino-3-pyridyl O n-pentyl OH2-morpholino-3-pyridyl O n-pentyl OH 4-morpholino-3-pyridyl O n-pentylOH 5-morpholino-3-pyridyl O n-pentyl OH 6-morpholino-3-pyridyl On-pentyl OH 2-hydroxy-3-pyridyl O n-pentyl OH 4-hydroxy-3-pyridyl On-pentyl OH 5-hydroxy-3-pyridyl O n-pentyl OH 6-hydroxy-3-pyridyl On-pentyl OH 2-mercapto-3-pyridyl O n-pentyl OH 4-mercapto-3-pyridyl On-pentyl OH 5-mercapto-3-pyridyl O n-pentyl OH 6-mercapto-3-pyridyl On-pentyl OH 2-methylthio-3-pyridyl O n-pentyl OH 4-methylthio-3-pyridylO n-pentyl OH 5-methylthio-3-pyridyl O n-pentyl OH6-methylthio-3-pyridyl O n-pentyl OH 2,6-dimethyl-3-pyridyl O n-pentylOH 5,6-dimethyl-3-pyridyl O n-pentyl OH 2,6-diethyl-3-pyridyl O n-pentylOH 5,6-diethyl-3-pyridyl O n-pentyl OH 2,6-dimethoxy-3-pyridyl On-pentyl OH 5,6-dimethoxy-3-pyridyl O n-pentyl OH 2,6-diethoxy-3-pyridylO n-pentyl OH 5,6-diethoxy-3-pyridyl O n-pentyl OH2,6-dichloro-3-pyridyl O n-pentyl OH 5,6-dichloro-3-pyridyl O n-pentylOH 5-chloro-6-methoxy-3-pyridyl O n-pentyl OH5-chloro-6-ethoxy-3-pyridyl O n-pentyl OH 2-chloro-6-methyl-3-pyridyl On-pentyl OH 6-chloro-2-methyl-3-pyridyl O n-pentyl OH 2-methyl-4-pyridylO n-pentyl OH 2-ethyl-4-pyridyl O n-pentyl OH 2-methoxy-4-pyridyl On-pentyl OH 2-ethoxy-4-pyridyl O n-pentyl OH 2-chloro-4-pyridyl On-pentyl OH 2-dimethylamino-4-pyridyl O n-pentyl OH2-(1-pyrrolidinyl)-4-pyridyl O n-pentyl OH 2-piperidino-4-pyridyl On-pentyl OH 2-morpholino-4-pyridyl O n-pentyl OH 2-methylthio-4-pyridylO n-pentyl OH 2-pyrazinyl O n-pentyl OH 5-methyl-2-pyrazinyl O n-pentylOH 5-ethyl-2-pyrazinyl O n-pentyl OH 5-methoxy-2-pyrazinyl O n-pentyl OH5-ethoxy-2-pyrazinyl O n-pentyl OH 5-chloro-2-pyrazinyl O n-pentyl OH6-methyl-2-pyrazinyl O n-pentyl OH 6-methoxy-2-pyrazinyl O n-pentyl OH6-chloro-2-pyrazinyl O n-pentyl OCOOMe 2-pyridyl O n-pentyl OCOOMe3-pyridyl O n-pentyl OCOOMe 4-pyridyl O n-pentyl OCOOMe2-methyl-3-pyridyl O n-pentyl OCOOMe 4-methyl-3-pyridyl O n-pentylOCOOMe 5-methyl-3-pyridyl O n-pentyl OCOOMe 6-methyl-3-pyridyl On-pentyl OCOOMe 2-ethyl-3-pyridyl O n-pentyl OCOOMe 4-ethyl-3-pyridyl On-pentyl OCOOMe 5-ethyl-3-pyridyl O n-pentyl OCOOMe 6-ethyl-3-pyridyl On-pentyl OCOOMe 2-methoxy-3-pyridyl O n-pentyl OCOOMe4-methoxy-3-pyridyl O n-pentyl OCOOMe 5-methoxy-3-pyridyl O n-pentylOCOOMe 6-methoxy-3-pyridyl O n-pentyl OCOOMe 2-ethoxy-3-pyridyl On-pentyl OCOOMe 4-ethoxy-3-pyridyl O n-pentyl OCOOMe 5-ethoxy-3-pyridylO n-pentyl OCOOMe 6-ethoxy-3-pyridyl O n-pentyl OCOOMe2-chloro-3-pyridyl O n-pentyl OCOOMe 4-chloro-3-pyridyl O n-pentylOCOOMe 5-chloro-3-pyridyl O n-pentyl OCOOMe 6-chloro-3-pyridyl On-pentyl OCOOMe 2-fluoro-3-pyridyl O n-pentyl OCOOMe 4-fluoro-3-pyridylO n-pentyl OCOOMe 5-fluoro-3-pyridyl O n-pentyl OCOOMe6-fluoro-3-pyridyl O n-pentyl OCOOMe 2-dimethylamino-3-pyridyl On-pentyl OCOOMe 4-dimethylamino-3-pyridyl O n-pentyl OCOOMe5-dimethylamino-3-pyridyl O n-pentyl OCOOMe 6-dimethylamino-3-pyridyl On-pentyl OCOOMe 2-(1-pyrrolidinyl)-3-pyridyl O n-pentyl OCOOMe3-(1-pyrrolidinyl)-3-pyridyl O n-pentyl OCOOMe5-(1-pyrrolidinyl)-3-pyridyl O n-pentyl OCOOMe6-(1-pyrrolidinyl)-3-pyridyl O n-pentyl OCOOMe 2-piperidino-3-pyridyl On-pentyl OCOOMe 4-piperidino-3-pyridyl O n-pentyl OCOOMe5-piperidino-3-pyridyl O n-pentyl OCOOMe 6-piperidino-3-pyridyl On-pentyl OCOOMe 2-morpholino-3-pyridyl O n-pentyl OCOOMe4-morpholino-3-pyridyl O n-pentyl OCOOMe 5-morpholino-3-pyridyl On-pentyl OCOOMe 6-morpholino-3-pyridyl O n-pentyl OCOOMe2-hydroxy-3-pyridyl O n-pentyl OCOOMe 4-hydroxy-3-pyridyl O n-pentylOCOOMe 5-hydroxy-3-pyridyl O n-pentyl OCOOMe 6-hydroxy-3-pyridyl On-pentyl OCOOMe 2-mercapto-3-pyridyl O n-pentyl OCOOMe4-mercapto-3-pyridyl O n-pentyl OCOOMe 5-mercapto-3-pyridyl O n-pentylOCOOMe 6-mercapto-3-pyridyl O n-pentyl OCOOMe 2-methylthio-3-pyridyl On-pentyl OCOOMe 4-methylthio-3-pyridyl O n-pentyl OCOOMe5-methylthio-3-pyridyl O n-pentyl OCOOMe 6-methylthio-3-pyridyl On-pentyl OCOOMe 2,6-dimethyl-3-pyridyl O n-pentyl OCOOMe5,6-dimethyl-3-pyridyl O n-pentyl OCOOMe 2,6-diethyl-3-pyridyl On-pentyl OCOOMe 5,6-diethyl-3-pyridyl O n-pentyl OCOOMe2,6-dimethoxy-3-pyridyl O n-pentyl OCOOMe 5,6-dimethoxy-3-pyridyl On-pentyl OCOOMe 2,6-diethoxy-3-pyridyl O n-pentyl OCOOMe5,6-diethoxy-3-pyridyl O n-pentyl OCOOMe 2,6-dichloro-3-pyridyl On-pentyl OCOOMe 5,6-dichloro-3-pyridyl O n-pentyl OCOOMe5-chloro-6-methoxy-3-pyridyl O n-pentyl OCOOMe5-chloro-6-methoxy-3-pyridyl O n-pentyl OCOOMe2-chloro-6-methyl-3-pyridyl O n-pentyl OCOOMe6-chloro-2-methyl-3-pyridyl O n-pentyl OCOOMe 2-methyl-4-pyridyl On-pentyl OCOOMe 2-ethyl-4-pyridyl O n-pentyl OCOOMe 2-methoxy-4-pyridylO n-pentyl OCOOMe 2-ethoxy-4-pyridyl O n-pentyl OCOOMe2-chloro-4-pyridyl O n-pentyl OCOOMe 2-dimethylamino-4-pyridyl On-pentyl OCOOMe 2-(1-pyrrolidinyl)-4-pyridyl O n-pentyl OCOOMe2-piperidino-4-pyridyl O n-pentyl OCOOMe 2-morpholino-4-pyridyl On-pentyl OCOOMe 2-methylthio-4-pyridyl O n-pentyl OCOOMe 2-pyrazinyl On-pentyl OCOOMe 5-methyl-2-pyrazinyl O n-pentyl OCOOMe5-ethyl-2-pyrazinyl O n-pentyl OCOOMe 5-methoxy-2-pyrazinyl O n-pentylOCOOMe 5-ethoxy-2-pyrazinyl O n-pentyl OCOOMe 5-chloro-2-pyrazinyl On-pentyl OCOOMe 6-methyl-2-pyrazinyl O n-pentyl OCOOMe6-methoxy-2-pyrazinyl O n-pentyl OCOOMe 6-chloro-2-pyrazinyl O n-pentylOCOOEt 2-pyridyl O n-pentyl OCOOEt 3-pyridyl O n-pentyl OCOOEt 4-pyridylO n-pentyl OCOOEt 2-methyl-3-pyridyl O n-pentyl OCOOEt4-methyl-3-pyridyl O n-pentyl OCOOEt 5-methyl-3-pyridyl O n-pentylOCOOEt 6-methyl-3-pyridyl O n-pentyl OCOOEt 2-ethyl-3-pyridyl O n-pentylOCOOEt 4-ethyl-3-pyridyl O n-pentyl OCOOEt 5-ethyl-3-pyridyl O n-pentylOCOOEt 6-ethyl-3-pyridyl O n-pentyl OCOOEt 2-methoxy-3-pyridyl On-pentyl OCOOEt 4-methoxy-3-pyridyl O n-pentyl OCOOEt5-methoxy-3-pyridyl O n-pentyl OCOOEt 6-methoxy-3-pyridyl O n-pentylOCOOEt 2-ethoxy-3-pyridyl O n-pentyl OCOOEt 4-ethoxy-8-pyridyl On-pentyl OCOOEt 5-ethoxy-3-pyridyl O n-pentyl OCOOEt 6-ethoxy-3-pyridylO n-pentyl OCOOEt 2-chloro-3-pyridyl O n-pentyl OCOOEt4-chloro-3-pyridyl O n-pentyl OCOOEt 5-chloro-3-pyridyl O n-pentylOCOOEt 6-chloro-3-pyridyl O n-pentyl OCOOEt 2-fluoro-3-pyridyl On-pentyl OCOOEt 4-fluoro-3-pyridyl O n-pentyl OCOOEt 5-fluoro-3-pyridylO n-pentyl OCOOEt 6-fluoro-3-pyridyl O n-pentyl OCOOEt2-dimethylamino-3-pyridyl O n-pentyl OCOOEt 4-dimethylamino-3-pyridyl On-pentyl OCOOEt 5-dimethylamino-3-pyridyl O n-pentyl OCOOEt6-dimethylamino-3-pyridyl O n-pentyl OCOOEt 2-(1-pyrrolidinyl)-3-pyridylO n-pentyl OCOOEt 3-(1-pyrrolidinyl)-3-pyridyl O n-pentyl OCOOEt5-(1-pyrrolidinyl)-3-pyridyl O n-pentyl OCOOEt6-(1-pyrrolidinyl)-3-pyridyl O n-pentyl OCOOEt 2-piperidino-3-pyridyl On-pentyl OCOOEt 4-piperidino-3-pyridyl O n-pentyl OCOOEt5-piperidino-3-pyridyl O n-pentyl OCOOEt 6-piperidino-3-pyridyl On-pentyl OCOOEt 2-morpholino-3-pyridyl O n-pentyl OCOOEt4-morpholino-3-pyridyl O n-pentyl OCOOEt 5-morpholino-3-pyridyl On-pentyl OCOOEt 6-morpholino-3-pyridyl O n-pentyl OCOOEt2-hydroxy-3-pyridyl O n-pentyl OCOOEt 4-hydroxy-3-pyridyl O n-pentylOCOOEt 5-hydroxy-3-pyridyl O n-pentyl OCOOEt 6-hydroxy-3-pyridyl On-pentyl OCOOEt 2-mercapto-3-pyridyl O n-pentyl OCOOEt4-mercapto-3-pyridyl O n-pentyl OCOOEt 5-mercapto-3-pyridyl O n-pentylOCOOEt 6-mercapto-3-pyridyl O n-pentyl OCOOEt 2-methylthio-3-pyridyl On-pentyl OCOOEt 4-methylthio-3-pyridyl O n-pentyl OCOOEt5-methylthio-3-pyridyl O n-pentyl OCOOEt 6-methylthio-3-pyridyl On-pentyl OCOOEt 2,6-dimethyl-3-pyridyl O n-pentyl OCOOEt5,6-dimethyl-3-pyridyl O n-pentyl OCOOEt 2,6-diethyl-3-pyridyl On-pentyl OCOOEt 5,6-diethyl-3-pyridyl O n-pentyl OCOOEt2,6-dimethoxy-3-pyridyl O n-pentyl OCOOEt 5,6-dimethoxy-3-pyridyl On-pentyl OCOOEt 2,6-diethoxy-3-pyridyl O n-pentyl OCOOEt5,6-diethoxy-3-pyridyl O n-pentyl OCOOEt 2,6-dichloro-3-pyridyl On-pentyl OCOOEt 5,6-dichloro-3-pyridyl O n-pentyl OCOOEt5-chloro-6-methoxy-3-pyridyl O n-pentyl OCOOEt5-chloro-6-ethoxy-3-pyridyl O n-pentyl OCOOEt2-chloro-6-methyl-3-pyridyl O n-pentyl OCOOEt6-chloro-2-methyl-3-pyridyl O n-pentyl OCOOEt 2-methyl-4-pyridyl On-pentyl OCOOEt 2-ethyl-4-pyridyl O n-pentyl OCOOEt 2-methoxy-4-pyridylO n-pentyl OCOOEt 2-ethoxy-4-pyridyl O n-pentyl OCOOEt2-chloro-4-pyridyl O n-pentyl OCOOEt 2-dimethylamino-4-pyridyl On-pentyl OCOOEt 2-(1-pyrrolidinyl)-4-pyridyl O n-pentyl OCOOEt2-piperidino-4-pyridyl O n-pentyl OCOOEt 2-morpholino-4-pyridyl On-pentyl OCOOEt 2-methylthio-4-pyridyl O n-pentyl OCOOEt 2-pyrazinyl On-pentyl OCOOEt 5-methyl-2-pyrazinyl O n-pentyl OCOOEt5-ethyl-2-pyrazinyl O n-pentyl OCOOEt 5-methoxy-2-pyrazinyl O n-pentylOCOOEt 5-ethoxy-2-pyrazinyl O n-pentyl OCOOEt 5-chloro-2-pyrazinyl On-pentyl OCOOEt 6-methyl-2-pyrazinyl O n-pentyl OCOOEt6-methoxy-2-pyrazinyl O n-pentyl OCOOEt 6-chloro-2-pyrazinyl S propyl OH2-pyridyl S propyl OH 3-pyridyl S propyl OH 4-pyridyl S propyl OH2-methyl-3-pyridyl S propyl OH 4-methyl-3-pyridyl S propyl OH5-methyl-3-pyridyl S propyl OH 6-methyl-3-pyridyl S propyl OH2-ethyl-3-pyridyl S propyl OH 4-ethyl-3-pyridyl S propyl OH5-ethyl-3-pyridyl S propyl OH 6-ethyl-3-pyridyl S propyl OH2-methoxy-3-pyridyl S propyl OH 4-methoxy-3-pyridyl S propyl OH5-methoxy-3-pyridyl S propyl OH 6-methoxy-3-pyridyl S propyl OH2-ethoxy-3-pyridyl S propyl OH 4-ethoxy-3-pyridyl S propyl OH5-ethoxy-3-pyridyl S propyl OH 6-ethoxy-3-pyridyl S propyl OH2-chloro-3-pyridyl S propyl OH 4-chloro-3-pyridyl S propyl OH5-chloro-3-pyridyl S propyl OH 6-chloro-3-pyridyl S propyl OH2-fluoro-3-pyridyl S propyl OH 4-fluoro-3-pyridyl S propyl OH5-fluoro-3-pyridyl S propyl OH 6-fluoro-3-pyridyl S propyl OH2-dimethylamino-3-pyridyl S propyl OH 4-dimethylamino-3-pyridyl S propylOH 5-dimethylamino-3-pyridyl S propyl OH 6-dimethylamino-3-pyridyl Spropyl OH 2-(1-pyrrolidinyl)-3-pyridyl S propyl OH3-(1-pyrrolidinyl)-3-pyridyl S propyl OH 5-(1-pyrrolidinyl)-3-pyridyl Spropyl OH 6-(1-pyrrolidinyl)-3-pyridyl S propyl OH2-piperidino-3-pyridyl S propyl OH 4-piperidino-3-pyridyl S propyl OH5-piperidino-3-pyridyl S propyl OH 6-piperidino-3-pyridyl S propyl OH2-morpholino-3-pyridyl S propyl OH 4-morpholino-3-pyridyl S propyl OH5-morpholino-3-pyridyl S propyl OH 6-morpholino-3-pyridyl S propyl OH2-hydroxy-3-pyridyl S propyl OH 4-hydroxy-3-pyridyl S propyl OH5-hydroxy-3-pyridyl S propyl OH 6-hydroxy-3-pyridyl S propyl OH2-mercapto-3-pyridyl S propyl OH 4-mercapto-3-pyridyl S propyl OH5-mercapto-3-pyridyl S propyl OH 6-mercapto-3-pyridyl S propyl OH2-methylthio-3-pyridyl S propyl OH 4-methylthio-3-pyridyl S propyl OH5-methylthio-3-pyridyl S propyl OH 6-methylthio-3-pyridyl S propyl OH2,6-dimethyl-3-pyridyl S propyl OH 5,6-dimethyl-3-pyridyl S propyl OH2,6-diethyl-3-pyridyl S propyl OH 5,6-diethyl-3-pyridyl S propyl OH2,6-dimethoxy-3-pyridyl S propyl OH 5,6-dimethoxy-3-pyridyl S propyl OH2,6-diethoxy-3-pyridyl S propyl OH 5,6-diethoxy-3-pyridyl S propyl OH2,6-dichloro-3-pyridyl S propyl OH 5,6-dichloro-3-pyridyl S propyl OH5-chloro-6-methoxy-3-pyridyl S propyl OH 5-chloro-6-ethoxy-3-pyridyl Spropyl OH 2-chloro-6-methyl-3-pyridyl S propyl OH6-chloro-2-methyl-3-pyridyl S propyl OH 2-methyl-4-pyridyl S propyl OH2-ethyl-4-pyridyl S propyl OH 2-methoxy-4-pyridyl S propyl OH2-ethoxy-4-pyridyl S propyl OH 2-chloro-4-pyridyl S propyl OH2-dimethylamino-4-pyridyl S propyl OH 2-(1-pyrrolidinyl)-4-pyridyl Spropyl OH 2-piperidino-4-pyridyl S propyl OH 2-morpholino-4-pyridyl Sprapyl OH 2-methylthio-4-pyridyl S propyl OH 2-pyrazinyl S propyl OH5-methyl-2-pyrazinyl S propyl OH 5-ethyl-2-pyrazinyl S propyl OH5-methoxy-2-pyrazinyl S propyl OH 5-ethoxy-2-pyrazinyl S propyl OH5-chloro-2-pyrazinyl S propyl OH 6-methyl-2-pyrazinyl S propyl OH6-methoxy-2-pyrazinyl S propyl OH 6-chloro-2-pyrazinyl S propyl OCOOMe2-pyridyl S propyl OCOOMe 3-pyridyl S propyl OCOOMe 4-pyridyl S propylOCOOMe 2-methyl-3-pyridyl S propyl OCOOMe 4-methyl-3-pyridyl S propylOCOOMe 5-methyl-3-pyridyl S propyl OCOOMe 6-methyl-3-pyridyl S propylOCOOMe 2-ethyl-3-pyridyl S propyl OCOOMe 4-ethyl-3-pyridyl S propylOCOOMe 5-ethyl-3-pyridyl S propyl OCOOMe 6-ethyl-3-pyridyl S propylOCOOMe 2-methoxy-3-pyridyl S propyl OCOOMe 4-methoxy-3-pyridyl S propylOCOOMe 5-methoxy-3-pyridyl S propyl OCOOMe 6-methoxy-3-pyridyl S propylOCOOMe 2-ethoxy-3-pyridyl S propyl OCOOMe 4-ethoxy-3-pyridyl S propylOCOOMe 5-ethoxy-3-pyridyl S propyl OCOOMe 6-ethoxy-3-pyridyl S propylOCOOMe 2-chloro-3-pyridyl S propyl OCOOMe 4-chloro-3-pyridyl S propylOCOOMe 5-chloro-3-pyridyl S propyl OCOOMe 6-chloro-3-pyridyl S propylOCOOMe 2-fluoro-3-pyridyl S propyl OCOOMe 4-fluoro-3-pyridyl S propylOCOOMe 5-fluoro-3-pyridyl S propyl OOOOMe 6-fluoro-3-pyridyl S propylOCOOMe 2-dimethylamino-3-pyridyl S propyl OCOOMe4-dimethylamino-3-pyridyl S propyl OCOOMe 5-dimethylamino-3-pyridyl Spropyl OCOOMe 6-dimethylamino-3-pyridyl S propyl OCOOMe2-(1-pyrrolidinyl)-3-pyridyl S propyl OCOOMe3-(1-pyrrolidinyl)-3-pyridyl S propyl OCOOMe5-(1-pyrrolidinyl)-3-pyridyl S propyl OCOOMe6-(1-pyrrolidinyl)-3-pyridyl S propyl OCOOMe 2-pipendino-3-pyridyl Spropyl OCOOMe 4-piperidino-3-pyridyl S propyl OCOOMe5-piperidino-3-pyridyl S propyl OCOOMe 6-piperidino-3-pyridyl S propylOCOOMe 2-morpholino-3-pyridyl S propyl OCOOMe 4-morpholino-3-pyridyl Spropyl OCOOMe 5-morpholino-3-pyridyl S propyl OCOOMe6-morpholino-3-pyridyl S propyl OCOOMe 2-hydroxy-3-pyridyl S propylOCOOMe 4-hydroxy-3-pyridyl S propyl OCOOMe 5-hydroxy-3-pyridyl S propylOCOOMe 6-hydroxy-3-pyridyl S propyl OCOOMe 2-mercapto-3-pyridyl S propylOCOOMe 4-mercapto-3-pyridyl S propyl OCOOMe 5-mercapto-3-pyridyl Spropyl OCOOMe 6-mercapto-3-pyridyl S propyl OCOOMe2-methylthio-3-pyridyl S propyl OCOOMe 4-methylthio-3-pyridyl S propylOCOOMe 5-methylthio-3-pyridyl S propyl OCOOMe 6-methylthio-3-pyridyl Spropyl OCOOMe 2,6-dimethyl-3-pyridyl S propyl OCOOMe5,6-dimethyl-3-pyridyl S propyl OCOOMe 2,6-diethyl-3-pyridyl S propylOCOOMe 5,6-diethyl-3-pyridyl S propyl OCOOMe 2,6-dimethoxy-3-pyridyl Spropyl OCOOMe 5,6-dimethoxy-3-pyridyl S propyl OCOOMe2,6-diethoxy-3-pyridyl S propyl OCOOMe 5,6-diethoxy-3-pyridyl S propylOCOOMe 2,6-dichloro-3-pyridyl S propyl OCOOMe 5,6-dichloro-3-pyridyl Spropyl OCOOMe 5-chloro-6-methoxy-3-pyridyl S propyl OCOOMe5-chloro-6-ethoxy-3-pyridyl S propyl OCOOMe 2-chloro-6-methyl-3-pyridylS propyl OCOOMe 6-chloro-2-methyl-3-pyridyl S propyl OCOOMe2-methyl-4-pyridyl S propyl OCOOMe 2-ethyl-4-pyridyl S propyl OCOOMe2-methoxy-4-pyridyl S propyl OCOOMe 2-ethoxy-4-pyridyl S propyl OCOOMe2-chloro-4-pyridyl S propyl OCOOMe 2-dimethylamino-4-pyridyl S propylOCOOMe 2-(1-pyrrolidinyl)-4-pyridyl S propyl OCOOMe2-piperidino-4-pyridyl S propyl OCOOMe 2-morpholino-4-pyridyl S propylOCOOMe 2-methylthio-4-pyridyl S propyl OCOOMe 2-pyrazinyl S propylOCOOMe 5-methyl-2-pyrazinyl S propyl OCOOMe 5-ethyl-2-pyrazinyl S propylOCOOMe 5-methoxy-2-pyrazinyl S propyl OCOOMe 5-ethoxy-2-pyrazinyl Spropyl OCOOMe 5-chloro-2-pyrazinyl S propyl OCOOMe 6-methyl-2-pyrazinylS propyl OCOOMe 6-methoxy-2-pyrazinyl S propyl OCOOMe6-chloro-2-pyrazinyl S propyl OCOOEt 2-pyridyl S propyl OCOOEt 3-pyridylS propyl OCOOEt 4-pyridyl S propyl OCOOEt 2-methyl-3-pyridyl S propylOCOOEt 4-methyl-3-pyridyl S propyl OCOOEt 5-methyl-3-pyridyl S propylOCOOEt 6-methyl-3-pyridyl S propyl OCOOEt 2-ethyl-3-pyridyl S propylOCOOEt 4-ethyl-3-pyridyl S propyl OCOOEt 5-ethyl-3-pyridyl S propylOCOOEt 6-ethyl-3-pyridyl S propyl OCOOEt 2-methoxy-3-pyridyl S propylOCOOEt 4-methoxy-3-pyridyl S propyl OCOOEt 5-methoxy-3-pyridyl S propylOCOOEt 6-methoxy-3-pyridyl S propyl OCOOEt 2-ethoxy-3-pyridyl S propylOCOOEt 4-ethoxy-3-pyridyl S propyl OCOOEt 5-ethoxy-3-pyridyl S propylOCOOEt 6-ethoxy-3-pyridyl S propyl OCOOEt 2-chloro-3-pyridyl S propylOCOOEt 4-chloro-3-pyridyl S propyl OCOOEt 5-chloro-3-pyridyl S propylOCOOEt 6-chloro-3-pyridyl S propyl OCOOEt 2-fluoro-3-pyridyl S propylOCOOEt 4-fluoro-3-pyridyl S propyl OCOOEt 5-fluoro-3-pyridyl S propylOCOOEt 6-fluoro-3-pyridyl S propyl OCOOEt 2-dimethylamino-3-pyridyl Spropyl OCOOEt 4-dimethylamino-3-pyridyl S propyl OCOOEt5-dimethylamino-3-pyridyl S propyl OCOOEt 6-dimethylamino-3-pyridyl Spropyl OCOOEt 2-(1-pyrrolidinyl)-3-pyridyl S propyl OCOOEt3-(1-pyrrolidinyl)-3-pyridyl S propyl OCOOEt5-(1-pyrrolidinyl)-3-pyridyl S propyl OCOOEt6-(1-pyrrolidinyl)-3-pyridyl S propyl OCOOEt 2-piperidino-3-pyridyl Spropyl OCOOEt 4-piperidino-3-pyridyl S propyl OCOOEt5-piperidino-3-pyridyl S propyl OCOOEt 6-piperidino-3-pyridyl S propylOCOOEt 2-morpholino-3-pyridyl S propyl OCOOEt 4-morpholino-3-pyridyl Spropyl OCOOEt 5-morpholino-3-pyridyl S propyl OCOOEt6-morpholino-3-pyridyl S propyl OCOOEt 2-hydroxy-3-pyridyl S propylOCOOEt 4-hydroxy-3-pyridyl S propyl OCOOEt 5-hydroxy-3-pyridyl S propylOCOOEt 6-hydroxy-3-pyridyl S propyl OCOOEt 2-mercapto-3-pyridyl S propylOCOOEt 4-mercapto-3-pyridyl S propyl OCOOEt 5-mercapto-3-pyridyl Spropyl OCOOEt 6-mercapto-3-pyridyl S propyl OCOOEt2-methylthio-3-pyridyl S propyl OCOOEt 4-methylthio-3-pyridyl S propylOCOOEt 5-methylthio-3-pyridyl S propyl OCOOEt 6-methylthio-3-pyridyl Spropyl OCOOEt 2,6-dimethyl-3-pyridyl S propyl OCOOEt5,6-dimethyl-3-pyridyl S propyl OCOOEt 2,6-diethyl-3-pyridyl S propylOCOOEt 5,6-diethyl-3-pyridyl S propyl OCOOEt 2,6-dimethoxy-3-pyridyl Spropyl OCOOEt 5,6-dimethoxy-3-pyridyl S propyl OCOOEt2,6-diethoxy-3-pyridyl S propyl OCOOEt 5,6-diethoxy-3-pyridyl S propylOCOOEt 2,6-dichloro-3-pyridyl S propyl OCOOEt 5,6-dichloro-3-pyridyl Spropyl OCOOEt 5-chloro-6-methoxy-3-pyridyl S propyl OCOOEt5-chloro-6-ethoxy-3-pyridyl S propyl OCOOEt 2-chloro-6-methyl-3-pyridylS propyl OCOOEt 6-chloro-2-methyl-3-pyridyl S propyl OCOOEt2-methyl-4-pyridyl S propyl OCOOEt 2-ethyl-4-pyridyl S propyl OCOOEt2-methoxy-4-pyridyl S propyl OCOOEt 2-ethoxy-4-pyridyl S propyl OCOOEt2-chloro-4-pyridyl S propyl OCOOEt 2-dimethylamino-4-pyridyl S propylOCOOEt 2-(1-pyrrolidinyl)-4-pyridyl S propyl OCOOEt2-piperidino-4-pyridyl S propyl OCOOEt 2-morpholino-4-pyridyl S propylOCOOEt 2-methylthio-4-pyridyl S propyl OCOOEt 2-pyrazinyl S propylOCOOEt 5-methyl-2-pyrazinyl S propyl OCOOEt 5-ethyl-2-pyrazinyl S propylOCOOEt 5-methoxy-2-pyrazinyl S propyl OCOOEt 5-ethoxy-2-pyrazinyl Spropyl OCOOEt 5-chloro-2-pyrazinyl S propyl OCOOEt 6-methyl-2-pyrazinylS propyl OCOOEt 6-methoxy-2-pyrazinyl S propyl OCOOEt6-chloro-2-pyrazinyl S n-butyl OH 2-pyridyl S n-butyl OH 3-pyridyl Sn-butyl OH 4-pyridyl S n-butyl OH 2-methyl-3-pyridyl S n-butyl OH4-methyl-3-pyridyl S n-butyl OH 5-methyl-3-pyridyl S n-butyl OH6-methyl-3-pyridyl S n-butyl OH 2-ethyl-3-pyridyl S n-butyl OH4-ethyl-3-pyridyl S n-butyl OH 5-ethyl-3-pyridyl S n-butyl OH6-ethyl-3-pyridyl S n-butyl OH 2-methoxy-3-pyridyl S n-butyl OH4-methoxy-3-pyridyl S n-butyl OH 5-methoxy-3-pyridyl S n-butyl OH6-methoxy-3-pyridyl S n-butyl OH 2-ethoxy-3-pyridyl S n-butyl OH4-ethoxy-3-pyridyl S n-butyl OH 5-ethoxy-3-pyridyl S n-butyl OH6-ethoxy-3-pyridyl S n-butyl OH 2-chloro-3-pyridyl S n-butyl OH4-chloro-3-pyridyl S n-butyl OH 5-chloro-3-pyridyl S n-butyl OH6-chloro-3-pyridyl S n-butyl OH 2-fluoro-3-pyridyl S n-butyl OH4-fluoro-3-pyridyl S n-butyl OH 5-fluoro-3-pyridyl S n-butyl OH6-fluoro-3-pyridyl S n-butyl OH 2-dimethylamino-3-pyridyl S n-butyl OH4-dimethylamino-3-pyridyl S n-butyl OH 5-dimethylamino-3-pyridyl Sn-butyl OH 6-dimethylamino-3-pyridyl S n-butyl OH2-(1-pyrrolidinyl)-3-pyridyl S n-butyl OH 3-(1-pyrrolidinyl)-3-pyridyl Sn-butyl OH 5-(1-pyrrolidinyl)-3-pyridyl S n-butyl OH6-(1-pyrrolidinyl)-3-pyridyl S n-butyl OH 2-piperidino-3-pyridyl Sn-butyl OH 4-piperidino-3-pyridyl S n-butyl OH 5-piperidino-3-pyridyl Sn-butyl OH 6-piperidino-3-pyridyl S n-butyl OH 2-morpholino-3-pyridyl Sn-butyl OH 4-morpholino-3-pyridyl S n-butyl OH 5-morpholino-3-pyridyl Sn-butyl OH 6-morpholino-3-pyridyl S n-butyl OH 2-hydroxy-3-pyridyl Sn-butyl OH 4-hydroxy-3-pyridyl S n-butyl OH 5-hydroxy-3-pyridyl Sn-butyl OH 6-hydroxy-3-pyridyl S n-butyl OH 2-mercapto-3-pyridyl Sn-butyl OH 4-mercapto-3-pyridyl S n-butyl OH 5-mercapto-3-pyridyl Sn-butyl OH 6-mercapto-3-pyridyl S n-butyl OH 2-methylthio-3-pyridyl Sn-butyl OH 4-methylthio-3-pyridyl S n-butyl OH 5-methylthio-3-pyridyl Sn-butyl OH 6-methylthio-3-pyridyl S n-butyl OH 2,6-dimethyl-3-pyridyl Sn-butyl OH 5,6-dimethyl-3-pyridyl S n-butyl OH 2,6-diethyl-3-pyridyl Sn-butyl OH 5,6-diethyl-3-pyridyl S n-butyl OH 2,6-dimethoxy-3-pyridyl Sn-butyl OH 5,6-dimethoxy-3-pyridyl S n-butyl OH 2,6-diethoxy-3-pyridyl Sn-butyl OH 5,6-diethoxy-3-pyridyl S n-butyl OH 2,6-dichloro-3-pyridyl Sn-butyl OH 5,6-dichloro-3-pyridyl S n-butyl OH5-chloro-6-methoxy-3-pyridyl S n-butyl OH 5-chloro-6-ethoxy-3-pyridyl Sn-butyl OH 2-chloro-6-methyl-3-pyridyl S n-butyl OH6-chloro-2-methyl-3-pyridyl S n-butyl OH 2-methyl-4-pyridyl S n-butyl OH2-ethyl-4-pyridyl S n-butyl OH 2-methoxy-4-pyridyl S n-butyl OH2-ethoxy-4-pyridyl S n-butyl OH 2-chloro-4-pyridyl S n-butyl OH2-dimethylamino-4-pyridyl S n-butyl OH 2-(1-pyrrolidinyl)-4-pyridyl Sn-butyl OH 2-piperidino-4-pyridyl S n-butyl OH 2-morpholino-4-pyridyl Sn-butyl OH 2-methylthio-4-pyridyl S n-butyl OH 2-pyrazinyl S n-butyl OH5-methyl-2-pyrazinyl S n-butyl OH 5-ethyl-2-pyrazinyl S n-butyl OH5-methoxy-2-pyrazinyl S n-butyl OH 5-ethoxy-2-pyrazinyl S n-butyl OH5-chloro-2-pyrazinyl S n-butyl OH 6-methyl-2-pyrazinyl S n-butyl OH6-methoxy-2-pyrazinyl S n-butyl OH 6-chloro-2-pyrazinyl S n-butyl OCOOMe2-pyridyl S n-butyl OCOOMe 3-pyridyl S n-butyl OCOOMe 4-pyridyl Sn-butyl OCOOMe 2-methyl-3-pyridyl S n-butyl OCOOMe 4-methyl-3-pyridyl Sn-butyl OCOOMe 5-methyl-3-pyridyl S n-butyl OCOOMe 6-methyl-3-pyridyl Sn-butyl OCOOMe 2-ethyl-3-pyridyl S n-butyl OCOOMe 4-ethyl-3-pyridyl Sn-butyl OCOOMe 5-ethyl-3-pyridyl S n-butyl OCOOMe 6-ethyl-3-pyridyl Sn-butyl OCOOMe 2-methoxy-8-pyridyl S n-butyl OCOOMe 4-methoxy-3-pyridylS n-butyl OCOOMe 5-methoxy-3-pyridyl S n-butyl OCOOMe6-methoxy-3-pyridyl S n-butyl OCOOMe 2-ethoxy-3-pyridyl S n-butyl OCOOMe4-ethoxy-3-pyridyl S n-butyl OCOOMe 5-ethoxy-3-pyridyl S n-butyl OCOOMe6-ethoxy-3-pyridyl S n-butyl OCOOMe 2-chloro-3-pyridyl S n-butyl OCOOMe4-chloro-3-pyridyl S n-butyl OCOOMe 5-chloro-3-pyridyl S n-butyl OCOOMe6-chloro-3-pyridyl S n-butyl OCOOMe 2-fluoro-3-pyridyl S n-butyl OCOOMe4-fluoro-3-pyridyl S n-butyl OCOOMe 5-fluoro-3-pyridyl S n-butyl OCOOMe6-fluoro-3-pyridyl S n-butyl OCOOMe 2-dimethylamino-3-pyridyl S n-butylOCOOMe 4-dimethylamino-3-pyridyl S n-butyl OCOOMe5-dimethylamino-3-pyridyl S n-butyl OCOOMe 6-dimethylamino-3-pyridyl Sn-butyl OCOOMe 2-(1-pyrrolidinyl)-3-pyridyl S n-butyl OCOOMe3-(1-pyrrolidinyl)-3-pyridyl S n-butyl OCOOMe5-(1-pyrrolidinyl)-3-pyridyl S n-butyl OCOOMe6-(1-pyrrolidinyl)-3-pyridyl S n-butyl OCOOMe 2-piperidino-3-pyridyl Sn-butyl OCOOMe 4-piperidino-3-pyridyl S n-butyl OCOOMe5-piperidino-3-pyridyl S n-butyl OCOOMe 6-piperidino-3-pyridyl S n-butylOCOOMe 2-morpholino-3-pyridyl S n-butyl OCOOMe 4-morpholino-3-pyridyl Sn-butyl OCOOMe 5-morpholino-3-pyridyl S n-butyl OCOOMe6-morpholino-3-pyridyl S n-butyl OCOOMe 2-hydroxy-3-pyridyl S n-butylOCOOMe 4-hydroxy-3-pyridyl S n-butyl OCOOMe 5-hydroxy-3-pyridyl Sn-butyl OCOOMe 6-hydroxy-3-pyridyl S n-butyl OCOOMe 2-mercapto-3-pyridylS n-butyl OCOOMe 4-mercapto-3-pyridyl S n-butyl OCOOMe5-mercapto-3-pyridyl S n-butyl OCOOMe 6-mercapto-3-pyridyl S n-butylOCOOMe 2-methylthio-3-pyridyl S n-butyl OCOOMe 4-methylthio-3-pyridyl Sn-butyl OCOOMe 5-methylthio-3-pyridyl S n-butyl OCOOMe6-methylthio-3-pyridyl S n-butyl OCOOMe 2,6-dimethyl-3-pyridyl S n-butylOCOOMe 5,6-dimethyl-3-pyridyl S n-butyl OCOOMe 2,6-diethyl-3-pyridyl Sn-butyl OCOOMe 5,6-diethyl-3-pyridyl S n-butyl OCOOMe2,6-dimethoxy-3-pyridyl S n-butyl OCOOMe 5,6-dimethoxy-3-pyridyl Sn-butyl OCOOMe 2,6-diethoxy-3-pyridyl S n-butyl OCOOMe5,6-diethoxy-3-pyridyl S n-butyl OCOOMe 2,6-dichloro-3-pyridyl S n-butylOCOOMe 5,6-dichloro-3-pyridyl S n-butyl OCOOMe5-chloro-6-methoxy-3-pyridyl S n-butyl OCOOMe5-chloro-6-ethoxy-3-pyridyl S n-butyl OCOOMe 2-chloro-6-methyl-3-pyridylS n-butyl OCOOMe 6-chloro-2-methyl-3-pyridyl S n-butyl OCOOMe2-methyl-4-pyridyl S n-butyl OCOOMe 2-ethyl-4-pyridyl S n-butyl OCOOMe2-methoxy-4-pyridyl S n-butyl OCOOMe 2-ethoxy-4-pyridyl S n-butyl OCOOMe2-chloro-4-pyridyl S n-butyl OCOOMe 2-dimethylamino-4-pyridyl S n-butylOCOOMe 2-(1-pyrrolidinyl)-4-pyridyl S n-butyl OCOOMe2-piperidino-4-pyridyl S n-butyl OCOOMe 2-morpholino-4-pyridyl S n-butylOCOOMe 2-methylthio-4-pyridyl S n-butyl OCOOMe 2-pyrazinyl S n-butylOCOOMe 5-methyl-2-pyrazinyl S n-butyl OCOOMe 5-ethyl-2-pyrazinyl Sn-butyl OCOOMe 5-methoxy-2-pyrazinyl S n-butyl OCOOMe5-ethoxy-2-pyrazinyl S n-butyl OCOOMe 5-chloro-2-pyrazinyl S n-butylOCOOMe 6-methyl-2-pyrazinyl S n-butyl OCOOMe 6-methoxy-2-pyrazinyl Sn-butyl OCOOMe 6-chloro-2-pyrazinyl S n-butyl OCOOEt 2-pyridyl S n-butylOCOOEt 3-pyridyl S n-butyl OCOOEt 4-pyridyl S n-butyl OCOOEt2-methyl-3-pyridyl S n-butyl OCOOEt 4-methyl-3-pyridyl S n-butyl OCOOEt5-methyl-3-pyridyl S n-butyl OCOOEt 6-methyl-3-pyridyl S n-butyl OCOOEt2-ethyl-3-pyridyl S n-butyl OCOOEt 4-ethyl-3-pyridyl S n-butyl OCOOEt5-ethyl-3-pyridyl S n-butyl OCOOEt 6-ethyl-3-pyridyl S n-butyl OCOOEt2-methoxy-3-pyridyl S n-butyl OCOOEt 4-methoxy-3-pyridyl S n-butylOCOOEt 5-methoxy-3-pyridyl S n-butyl OCOCEt 6-methoxy-3-pyridyl Sn-butyl OCOOEt 2-ethoxy-3-pyridyl S n-butyl OCOOEt 4-ethoxy-3-pyridyl Sn-butyl OCOOEt 5-ethoxy-3-pyridyl S n-butyl OCOOEt 6-ethoxy-3-pyridyl Sn-butyl OCOOEt 2-chloro-3-pyridyl S n-butyl OCOOEt 4-chloro-3-pyridyl Sn-butyl OCOOEt 5-chloro-3-pyridyl S n-butyl OCOOEt 6-chloro-3-pyridyl Sn-butyl OCOOEt 2-fluoro-3-pyridyl S n-butyl OCOOEt 4-fluoro-3-pyridyl Sn-butyl OCOOEt 5-fluoro-3-pyridyl S n-butyl OCOOEt 6-fluoro-3-pyridyl Sn-butyl OCOOEt 2-dimethylamino-3-pyridyl S n-butyl OCOOEt4-dimethylamino-3-pyridyl S n-butyl OCOOEt 5-dimethylamino-3-pyridyl Sn-butyl OCOOEt 6-dimethylamino-3-pyridyl S n-butyl OCOOEt2-(1-pyrrolidinyl)-3-pyridyl S n-butyl OCCOEt3-(1-pyrrolidinyl)-3-pyridyl S n-butyl OCOOEt5-(1-pyrrolidinyl)-3-pyridyl S n-butyl OCOOEt6-(1-pyrrolidinyl)-3-pyridyl S n-butyl OCOOEt 2-piperidino-3-pyridyl Sn-butyl OCOOEt 4-piperidino-3-pyridyl S n-butyl OCOOEt5-piperidino-3-pyridyl S n-butyl OCOOEt 6-piperidinio-3-pyridyl Sn-butyl OCOOEt 2-morpholino-3-pyridyl S n-butyl OCOOEt4-morpholino-3-pyridyl S n-butyl OCOOEt 5-morpholino-3-pyridyl S n-butylOCOOEt 6-morpholino-3-pyridyl S n-butyl OCOOEt 2-hydroxy-3-pyridyl Sn-butyl OCOOEt 4-hydroxy-3-pyridyl S n-butyl OCOOEt 5-hydroxy-3-pyridylS n-butyl OCOOEt 6-hydroxy-3-pyridyl S n-butyl OCOOEt2-mercapto-3-pyridyl S n-butyl OCOOEt 4-mercapto-3-pyridyl S n-butylOCOOEt 5-mercapto-3-pyridyl S n-butyl OCOOEt 6-mercapto-3-pyridyl Sn-butyl OCOOEt 2-methylthio-3-pyridyl S n-butyl OCOOEt4-methylthio-3-pyridyl S n-butyl OCOOEt 5-methylthio-3-pyridyl S n-butylOCOOEt 6-methylthio-3-pyridyl S n-butyl OCOOEt 2,6-dimethyl-3-pyridyl Sn-butyl OCOOEt 5,6-dimethyl-3-pyridyl S n-butyl OCOOEt2,6-diethyl-3-pyridyl S n-butyl OCOOEt 5,6-diethyl-3-pyridyl S n-butylOCOOEt 2,6-dimethoxy-3-pyridyl S n-butyl OCOOEt 5,6-dimethoxy-3-pyridylS n-butyl OCOOEt 2,6-diethoxy-3-pyridyl S n-butyl OCOOEt5,6-diethoxy-3-pyridyl S n-butyl OCOOEt 2,6-dichloro-3-pyridyl S n-butylOCOOEt 5,6-dichloro-3-pyridyl S n-butyl OCOOEt5-chloro-6-methoxy-3-pyridyl S n-butyl OCOOEt5-chloro-6-ethoxy-3-pyridyl S n-butyl OCOOEt 2-chloro-6-methyl-3-pyridylS n-butyl OCOOEt 6-chloro-2-methyl-3-pyridyl S n-butyl OCOOEt2-methyl-4-pyridyl S n-butyl OCOOEt 2-ethyl-4-pyridyl S n-butyl OCOOEt2-methoxy-4-pyridyl S n-butyl OCOOEt 2-ethoxy-4-pyridyl S n-butyl OCOOEt2-chloro-4-pyridyl S n-butyl OCOOEt 2-dimethylamino-4-pyridyl S n-butylOCOOEt 2-(1-pyrrolidinyl)-4-pyridyl S n-butyl OCOOEt2-piperidino-4-pyridyl S n-butyl OCOOEt 2-morpholino-4-pyridyl S n-butylOCOOEt 2-methylthio-4-pyridyl S n-butyl OCOOEt 2-pyrazinyl S n-butylOCOOEt 5-methyl-2-pyrazinyl S n-butyl OCOOEt 5-ethyl-2-pyrazinyl Sn-butyl OCOOEt 5-methoxy-2-pyrazinyl S n-butyl OCOOEt5-ethoxy-2-pyrazinyl S n-butyl OCOOEt 5-chloro-2-pyrazinyl S n-butylOCOOEt 6-methyl-2-pyrazinyl S n-butyl OCOOEt 6-methoxy-2-pyrazinyl Sn-butyl OCOOEt 6-chloro-2-pyrazinyl S n-pentyl OH 2-pyridyl S n-pentylOH 3-pyridyl S n-pentyl OH 4-pyridyl S n-pentyl OH 2-methyl-3-pyridyl Sn-pentyl OH 4-methyl-3-pyridyl S n-pentyl OH 5-methyl-3-pyridyl Sn-pentyl OH 6-methyl-3-pyridyl S n-pentyl OH 2-ethyl-3-pyridyl Sn-pentyl OH 4-ethyl-3-pyridyl S n-pentyl OH 5-ethyl-3-pyridyl S n-pentylOH 6-ethyl-3-pyridyl S n-pentyl OH 2-methoxy-3-pyridyl S n-pentyl OH4-methoxy-3-pyridyl S n-pentyl OH 5-methoxy-3-pyridyl S n-pentyl OH6-methoxy-3-pyridyl S n-pentyl OH 2-ethoxy-3-pyridyl S n-pentyl OH4-ethoxy-3-pyridyl S n-pentyl OH 5-ethoxy-3-pyridyl S n-pentyl OH6-ethoxy-3-pyridyl S n-pentyl OH 2-chloro-3-pyridyl S n-pentyl OH4-chloro-3-pyridyl S n-pentyl OH 5-chloro-3-pyridyl S n-pentyl OH6-chloro-3-pyridyl S n-pentyl OH 2-fluoro-3-pyridyl S n-pentyl OH4-fluoro-3-pyridyl S n-pentyl OH 5-fluoro-3-pyridyl S n-pentyl OH6-fluoro-3-pyridyl S n-pentyl OH 2-dimethylamino-3-pyridyl S n-pentyl OH4-dimethylamino-3-pyridyl S n-pentyl OH 5-dimethylamino-3-pyridyl Sn-pentyl OH 6-dimethylamino-3-pyridyl S n-pentyl OH2-(1-pyrrolidinyl)-3-pyridyl S n-pentyl OH 3-(1-pyrrolidinyl)-3-pyridylS n-pentyl OH 5-(1-pyrrolidinyl)-3-pyridyl S n-pentyl OH6-(1-pyrrolidinyl)-3-pyridyl S n-pentyl OH 2-piperidino-3-pyridyl Sn-pentyl OH 4-piperidino-3-pyridyl S n-pentyl OH 5-piperidino-3-pyridylS n-pentyl OH 6-piperidino-3-pyridyl S n-pentyl OH2-morpholino-3-pyridyl S n-pentyl OH 4-morpholino-3-pyridyl S n-pentylOH 5-morpholino-3-pyridyl S n-pentyl OH 6-morpholino-3-pyridyl Sn-pentyl OH 2-hydroxy-3-pyridyl S n-pentyl OH 4-hydroxy-3-pyridyl Sn-pentyl OH 5-hydroxy-3-pyridyl S n-pentyl OH 6-hydroxy-3-pyridyl Sn-pentyl OH 2-mercapto-3-pyridyl S n-pentyl OH 4-mercapto-3-pyridyl Sn-pentyl OH 5-mercapto-3-pyridyl S n-pentyl OH 6-mercapto-3-pyridyl Sn-pentyl OH 2-methylthio-3-pyridyl S n-pentyl OH 4-methylthio-3-pyridylS n-pentyl OH 5-methylthio-3-pyridyl S n-pentyl OH6-methylthio-3-pyridyl S n-pentyl OH 2,6-dimethyl-3-pyridyl S n-pentylOH 5,6-dimethyl-3-pyridyl S n-pentyl OH 2,6-diethyl-3-pyridyl S n-pentylOH 5,6-diethyl-3-pyridyl S n-pentyl OH 2,6-dimethoxy-3-pyridyl Sn-pentyl OH 5,6-dimethoxy-3-pyridyl S n-pentyl OH 2,6-diethoxy-3-pyridylS n-pentyl OH 5,6-diethoxy-3-pyridyl S n-pentyl OH2,6-dichloro-3-pyridyl S n-pentyl OH 5,6-dichloro-3-pyridyl S n-pentylOH 5-chloro-6-methoxy-3-pyridyl S n-pentyl OH5-chloro-6-ethoxy-3-pyridyl S n-pentyl OH 2-chloro-6-methyl-3-pyridyl Sn-pentyl OH 6-chloro-2-methyl-3-pyridyl S n-pentyl OH 2-methyl-4-pyridylS n-pentyl OH 2-ethyl-4-pyridyl S n-pentyl OH 2-methoxy-4-pyridyl Sn-pentyl OH 2-ethoxy-4-pyridyl S n-pentyl OH 2-chloro-4-pyridyl Sn-pentyl OH 2-dimethylamino-4-pyridyl S n-pentyl OH2-(1-pyrrolidinyl)-4-pyridyl S n-pentyl OH 2-piperidino-4-pyridyl Sn-pentyl OH 2-morpholino-4-pyridyl S n-pentyl OH 2-methylthio-4-pyridylS n-pentyl OH 2-pyrazinyl S n-pentyl OH 5-methyl-2-pyrazinyl S n-pentylOH 5-ethyl-2-pyrazinyl S n-pentyl OH 5-methoxy-2-pyrazinyl S n-pentyl OH5-ethoxy-2-pyrazinyl S n-pentyl OH 5-chloro-2-pyrazinyl S n-pentyl OH6-methyl-2-pyrazinyl S n-pentyl OH 6-methoxy-2-pyrazinyl S n-pentyl OH6-chloro-2-pyrazinyl S n-pentyl OCOOMe 2-pyridyl S n-pentyl OCOOMe3-pyridyl S n-pentyl OCOOMe 4-pyridyl S n-pentyl OCOOMe2-methyl-3-pyridyl S n-pentyl OCOOMe 4-methyl-3-pyridyl S n-pentylOCOOMe 5-methyl-3-pyridyl S n-pentyl OCOOMe 6-methyl-3-pyridyl Sn-pentyl OCOOMe 2-ethyl-3-pyridyl S n-pentyl OCOOMe 4-ethyl-3-pyridyl Sn-pentyl OCOOMe 5-ethyl-3-pyridyl S n-pentyl OCOOMe 6-ethyl-3-pyridyl Sn-pentyl OCOOMe 2-methoxy-3-pyridyl S n-pentyl OCOOMe4-methoxy-3-pyridyl S n-pentyl OCOOMe 5-methoxy-3-pyridyl S n-pentylOCOOMe 6-methoxy-3-pyridyl S n-pentyl OCOOMe 2-ethoxy-3-pyridyl Sn-pentyl OCOOMe 4-ethoxy-3-pyridyl S n-pentyl OCOOMe 5-ethoxy-3-pyridylS n-pentyl OCOOMe 6-ethoxy-3-pyridyl S n-pentyl OCOOMe2-chloro-3-pyridyl S n-pentyl OCOOMe 4-chloro-3-pyridyl S n-pentylOCOOMe 5-chloro-3-pyridyl S n-pentyl OCOOMe 6-chloro-3-pyridyl Sn-pentyl OCOOMe 2-fluoro-3-pyridyl S n-pentyl OCOOMe 4-fluoro-3-pyridylS n-pentyl OCOOMe 5-fluoro-3-pyridyl S n-pentyl OCOOMe6-fluoro-3-pyridyl S n-pentyl OCOOMe 2-dimethylamino-3-pyridyl Sn-pentyl OCOOMe 4-dimethylamino-3-pyridyl S n-pentyl OCOOMe5-dimethylamino-3-pyridyl S n-pentyl OCOOMe 6-dimethylamino-3-pyridyl Sn-pentyl OCOOMe 2-(1-pyrrolidinyl)-3-pyridyl S n-pentyl OCOOMe3-(1-pyrrolidinyl)-3-pyridyl S n-pentyl OCOOMe5-(1-pyrrolidinyl)-3-pyridyl S n-pentyl OCOOMe6-(1-pyrrolidinyl)-3-pyridyl S n-pentyl OCOOMe 2-piperidino-3-pyridyl Sn-pentyl OCOOMe 4-piperidino-3-pyridyl S n-pentyl OCOOMe5-piperidino-3-pyridyl S n-pentyl OCOOMe 6-piperidino-3-pyridyl Sn-pentyl OCOOMe 2-morpholino-3-pyridyl S n-pentyl OCOOMe4-morpholino-3-pyridyl S n-pentyl OCOOMe 5-morpholino-3-pyridyl Sn-pentyl OCOOMe 6-morpholino-3-pyridyl S n-pentyl OCOOMe2-hydroxy-3-pyridyl S n-pentyl OCOOMe 4-hydroxy-3-pyridyl S n-pentylOCOOMe 5-hydroxy-3-pyridyl S n-pentyl OCOOMe 6-hydroxy-3-pyridyl Sn-pentyl OCOOMe 2-mercapto-3-pyridyl S n-pentyl OCOOMe4-mercapto-3-pyridyl S n-pentyl OCOOMe 5-mercapto-3-pyridyl S n-pentylOCOOMe 6-mercapto-3-pyridyl S n-pentyl OCOOMe 2-methylthio-3-pyridyl Sn-pentyl OCOOMe 4-methylthio-3-pyridyl S n-pentyl OCOOMe5-methylthio-3-pyridyl S n-pentyl OCOOMe 6-methylthio-3-pyridyl Sn-pentyl OCOOMe 2,6-dimethyl-3-pyridyl S n-pentyl OCOOMe5,6-dimethyl-3-pyridyl S n-pentyl OCOOMe 2,6-diethyl-3-pyridyl Sn-pentyl OCOOMe 5,6-diethyl-3-pyridyl S n-pentyl OCOOMe2,6-dimethoxy-3-pyridyl S n-pentyl OCOOMe 5,6-dimethoxy-3-pyridyl Sn-pentyl OCOOMe 2,6-diethoxy-3-pyridyl S n-pentyl OCOOMe5,6-diethoxy-3-pyridyl S n-pentyl OCOOMe 2,6-dichloro-3-pyridyl Sn-pentyl OCOOMe 5,6-dichloro-3-pyridyl S n-pentyl OCOOMe5-chloro-6-methoxy-3-pyridyl S n-pentyl OCOOMe5-chloro-6-ethoxy-3-pyridyl S n-pentyl OCOOMe2-chloro-6-methyl-3-pyridyl S n-pentyl OCOOMe6-chloro-2-methyl-3-pyridyl S n-pentyl OCOOMe 2-methyl-4-pyridyl Sn-pentyl OCOOMe 2-ethyl-4-pyridyl S n-pentyl OCOOMe 2-methoxy-4-pyridylS n-pentyl OCOOMe 2-ethoxy-4-pyridyl S n-pentyl OCOOMe2-chloro-4-pyridyl S n-pentyl OCOOMe 2-dimethylamino-4-pyridyl Sn-pentyl OCOOMe 2-(1-pyrrolidinyl)-4-pyridyl S n-pentyl OCOOMe2-piperidino-4-pyridyl S n-pentyl OCOOMe 2-morpholino-4-pyridyl Sn-pentyl OCOOMe 2-methylthio-4-pyridyl S n-pentyl OCOOMe 2-pyrazinyl Sn-pentyl OCOOMe 5-methyl-2-pyrazinyl S n-pentyl OCOOMe5-ethyl-2-pyrazinyl S n-pentyl OCOOMe 5-methoxy-2-pyrazinyl S n-pentylOCOOMe 5-ethoxy-2-pyrazinyl S n-pentyl OCOOMe 5-chloro-2-pyrazinyl Sn-pentyl OCOOMe 6-methyl-2-pyrazinyl S n-pentyl OCOOMe6-methoxy-2-pyrazinyl S n-pentyl OCOOMe 6-chloro-2-pyrazinyl S n-pentylOCOOEt 2-pyridyl S n-pentyl OCOOEt 3-pyridyl S n-pentyl OCOOEt 4-pyridylS n-pentyl OCOOEt 2-methyl-3-pyridyl S n-pentyl OCOOEt4-methyl-3-pyridyl S n-pentyl OCOOEt 5-methyl-3-pyridyl S n-pentylOCOOEt 6-methyl-3-pyridyl S n-pentyl OCOOEt 2-ethyl-3-pyridyl S n-pentylOCOOEt 4-ethyl-3-pyridyl S n-pentyl OCOOEt 5-ethyl-3-pyridyl S n-pentylOCOOEt 6-ethyl-3-pyridyl S n-pentyl OCOOEt 2-methoxy-3-pyridyl Sn-pentyl OCOOEt 4-methoxy-3-pyridyl S n-pentyl OCOOEt5-methoxy-3-pyridyl S n-pentyl OCOOEt 6-methoxy-3-pyridyl S n-pentylOCOOEt 2-ethoxy-3-pyridyl S n-pentyl OCOOEt 4-ethoxy-3-pyridyl Sn-pentyl OCOOEt 5-ethoxy-3-pyridyl S n-pentyl OCOOEt 6-ethoxy-3-pyridylS n-pentyl OCOOEt 2-chloro-3-pyridyl S n-pentyl OCOOEt4-chloro-3-pyridyl S n-pentyl OCOOEt 5-chloro-3-pyridyl S n-pentylOCOOEt 6-chloro-3-pyridyl S n-pentyl OCOOEt 2-fluoro-3-pyridyl Sn-pentyl OCOOEt 4-fluoro-3-pyridyl S n-pentyl OCOOEt 5-fluoro-3-pyridylS n-pentyl OCOOEt 6-fluoro-3-pyridyl S n-pentyl OCOOEt2-dimethylamino-3-pyridyl S n-pentyl OCOOEt 4-dimethylamino-3-pyridyl Sn-pentyl OCOOEt 5-dimethylamino-3-pyridyl S n-pentyl OCOOEt6-dimethylamino-3-pyridyl S n-pentyl OCOOEt 2-(1-pyrrolidinyl)-3-pyridylS n-pentyl OCOOEt 3-(1-pyrrolidinyl)-3-pyridyl S n-pentyl OCOOEt5-(1-pyrrolidinyl)-3-pyridyl S n-pentyl OCOOEt6-(1-pyrrolidinyl)-3-pyridyl S n-pentyl OCOOEt 2-piperidino-3-pyridyl Sn-pentyl OCOOEt 4-piperidino-3-pyridyl S n-pentyl OCOOEt5-piperidino-3-pyridyl S n-pentyl OCOOEt 6-piperidino-3-pyridyl Sn-pentyl OCOOEt 2-morpholino-3-pyridyl S n-pentyl OCOOEt4-morpholino-3-pyridyl S n-pentyl OCOOEt 5-morpholino-3-pyridyl Sn-pentyl OCOOEt 6-morpholino-3-pyridyl S n-pentyl OCOOEt2-hydroxy-3-pyridyl S n-pentyl OCOOEt 4-hydroxy-3-pyridyl S n-pentylOCOOEt 5-hydroxy-3-pyridyl S n-pentyl OCOOEt 6-hydroxy-3-pyridyl Sn-pentyl OCOOEt 2-mercapto-3-pyridyl S n-pentyl OCOOEt4-mercapto-3-pyridyl S n-pentyl OCOOEt 5-mercapto-3-pyridyl S n-pentylOCOOEt 6-mercapto-3-pyridyl S n-pentyl OCOOEt 2-methylthio-3-pyridyl Sn-pentyl OCOOEt 4-methylthio-3-pyridyl S n-pentyl OCOOEt5-methylthio-3-pyridyl S n-pentyl OCOOEt 6-methylthio-3-pyridyl Sn-pentyl OCOOEt 2,6-dimethyl-3-pyridyl S n-pentyl OCOOEt5,6-dimethyl-3-pyridyl S n-pentyl OCOOEt 2,6-diethyl-3-pyridyl Sn-pentyl OCOOEt 5,6-diethyl-3-pyridyl S n-pentyl OCOOEt2,6-dimethoxy-3-pyridyl S n-pentyl OCOOEt 5,6-dimethoxy-3-pyridyl Sn-pentyl OCOOEt 2,6-diethoxy-3-pyridyl S n-pentyl OCOOEt5,6-diethoxy-3-pyridyl S n-pentyl OCOOEt 2,6-dichloro-3-pyridyl Sn-pentyl OCOOEt 5,6-dichloro-3-pyridyl S n-pentyl OCOOEt5-chloro-6-methoxy-3-pyridyl S n-pentyl OCOOEt5-chloro-6-ethoxy-3-pyridyl S n-pentyl OCOOEt2-chloro-6-methyl-3-pyridyl S n-pentyl OCOOEt6-chloro-2-methyl-3-pyridyl S n-pentyl OCOOEt 2-methyl-4-pyridyl Sn-pentyl OCOOEt 2-ethyl-4-pyridyl S n-pentyl OCOOEt 2-methoxy-4-pyridylS n-pentyl OCOOEt 2-ethoxy-4-pyridyl S n-pentyl OCOOEt2-chloro-4-pyridyl S n-pentyl OCOOEt 2-dimethylamino-4-pyridyl Sn-pentyl OCOOEt 2-(1-pyrrolidinyl)-4-pyridyl S n-pentyl OCOOEt2-piperidino-4-pyridyl S n-pentyl OCOOEt 2-morpholino-4-pyridyl Sn-pentyl OCOOEt 2-methylthio-4-pyridyl S n-pentyl OCOOEt 2-pyrazinyl Sn-pentyl OCOOEt 5-methyl-2-pyrazinyl S n-pentyl OCOOEt5-ethyl-2-pyrazinyl S n-pentyl OCOOEt 5-methoxy-2-pyrazinyl S n-pentylOCOOEt 5-ethoxy-2-pyrazinyl S n-pentyl OCOOEt 5-chloro-2-pyrazinyl Sn-pentyl OCOOEt 6-methyl-2-pyrazinyl S n-pentyl OCOOEt6-methoxy-2-pyrazinyl S n-pentyl OCOOEt 6-chloro-2-pyrazinyl NH2-methoxyethyl OH 3-pyridyl NH 2-methoxyethyl OH 4-pyridyl NH2-methoxyethyl OH 2-methyl-3-pyridyl NH 2-methoxyethyl OH6-methyl-3-pyridyl NH 2-methoxyethyl OH 2-ethyl-3-pyridyl NH2-methoxyethyl OH 6-ethyl-3-pyridyl NH 2-methoxyethyl OH6-methoxy-3-pyridyl NH 2-methoxyethyl OH 6-ethoxy-3-pyridyl NH2-methoxyethyl OH 2-chloro-3-pyridyl NH 2-methoxyethyl OH6-chloro-3-pyridyl NH 2-methoxyethyl OH 5,6-dimethyl-3-pyridyl NH2-methoxyethyl OH 5,6-dimethoxy-3-pyridyl NH 2-methoxyethyl OH5,6-dichloro-3-pyridyl NH 2-methoxyethyl OH 6-dimethylamino-3-pyridyl NH2-methoxyethyl OH 6-(1-pyrrolidinyl)-3-pyridyl NH 2-methoxyethyl OH6-piperidino-3-pyridyl NH 2-methoxyethyl OH 6-morpholino-3-pyridyl NH2-methoxyethyl OH 6-methylthio-3-pyridyl NH 2-methoxyethyl OH2-pyrazinyl NH 2-methoxyethyl OH 5-methyl-2-pyrazinyl NH 3-methoxypropylOH 3-pyridyl NH 3-methoxypropyl OH 4-pyridyl NH 3-methoxypropyl OH2-methyl-3-pyridyl NH 3-methoxypropyl OH 6-methyl-3-pyridyl NH3-methoxypropyl OH 2-ethyl-3-pyridyl NH 3-methoxypropyl OH6-ethyl-3-pyridyl NH 3-methoxypropyl OH 2-methoxy-3-pyridyl NH3-methoxypropyl OH 6-methoxy-3-pyridyl NH 3-methoxypropyl OH6-ethoxy-3-pyridyl NH 3-methoxypropyl OH 2-chloro-3-pyridyl NH3-methoxypropyl OH 6-chloro-3-pyridyl NH 3-methoxypropyl OH5,6-dimethyl-3-pyridyl NH 3-methoxypropyl OH 5,6-dimethoxy-3-pyridyl NH3-methoxypropyl OH 5,6-dichloro-3-pyridyl NH 3-methoxypropyl OH6-dimethylamino-3-pyridyl NH 3-methoxypropyl OH6-(1-pyrrolidinyl)-3-pyridyl NH 3-methoxypropyl OH6-piperidino-3-pyridyl NH 3-methoxypropyl OH 6-morpholino-3-pyridyl NH3-methoxypropyl OH 6-methylthio-3-pyridyl NH 3-methoxypropyl OH2-pyrazinyl NH 3-methoxypropyl OH 5-methyl-2-pyrazinyl O 2-methoxyethylOH 3-pyridyl O 2-methoxyethyl OH 4-pyridyl O 2-methoxyethyl OH2-methyl-3-pyridyl O 2-methoxyethyl OH 6-methyl-3-pyridyl O2-methoxyethyl OH 2-ethyl-3-pyridyl O 2-methoxyethyl OH6-ethyl-3-pyridyl O 2-methoxyethyl OH 6-methoxy-3-pyridyl O2-methoxyethyl OH 6-ethoxy-3-pyridyl O 2-methoxyethyl OH2-chloro-3-pyridyl O 2-methoxyethyl OH 6-chloro-3-pyridyl O2-methoxyethyl OH 5,6-dimethyl-3-pyridyl O 2-methoxyethyl OH5,6-dimethoxy-3-pyridyl O 2-methoxyethyl OH 5,6-dichloro-3-pyridyl O2-methoxyethyl OH 6-dimethylamino-3-pyridyl O 2-methoxyethyl OH6-(1-pyrrolidinyl)-3-pyridyl O 2-methoxyethyl OH 6-piperidino-3-pyridylO 2-methoxyethyl OH 6-morpholino-3-pyridyl O 2-methoxyethyl OH6-methylthio-3-pyridyl O 2-methoxyethyl OH 2-pyrazinyl O 2-methoxyethylOH 5-methyl-2-pyrazinyl O 3-methoxypropyl OH 3-pyridyl O 3-methoxypropylOH 4-pyridyl O 3-methoxypropyl OH 2-methyl-3-pyridyl O 3-methoxypropylOH 6-methyl-3-pyridyl O 3-methoxypropyl OH 2-ethyl-3-pyridyl O3-methoxypropyl OH 6-ethyl-3-pyridyl O 3-methoxypropyl OH2-methoxy-3-pyridyl O 3-methoxypropyl OH 6-methoxy-3-pyridyl O3-methoxypropyl OH 6-ethoxy-3-pyridyl O 3-methoxypropyl OH2-chloro-3-pyridyl O 3-methoxypropyl OH 6-chloro-3-pyridyl O3-methoxypropyl OH 5,6-dimethyl-3-pyridyl O 3-methoxypropyl OH5,6-dimethoxy-3-pyridyl O 3-methoxypropyl OH 5,6-dichloro-3-pyridyl O3-methoxypropyl OH 6-dimethylamino-3-pyridyl O 3-methoxypropyl OH6-(1-pyrrolidinyl)-3-pyridyl O 3-methoxypropyl OH 6-piperidino-3-pyridylO 3-methoxypropyl OH 6-morpholino-3-pyridyl O 3-methoxypropyl OH6-methylthio-3-pyridyl O 3-methoxypropyl OH 2-pyrazinyl O3-methoxypropyl OH 5-methyl-2-pyrazinyl S 2-methoxyethyl OH 3-pyridyl S2-methoxyethyl OH 4-pyridyl S 2-methoxyethyl OH 2-methyl-3-pyridyl S2-methoxyethyl OH 6-methyl-3-pyridyl S 2-methoxyethyl OH2-ethyl-3-pyridyl S 2-methoxyethyl OH 6-ethyl-3-pyridyl S 2-methoxyethylOH 6-methoxy-3-pyridyl S 2-methoxyethyl OH 6-ethoxy-3-pyridyl S2-methoxyethyl OH 2-chloro-3-pyridyl S 2-methoxyethyl OH6-chloro-3-pyridyl S 2-methoxyethyl OH 5,6-dimethyl-3-pyridyl S2-methoxyethyl OH 5,6-dimethoxy-3-pyridyl S 2-methoxyethyl OH5,6-dichloro-3-pyridyl S 2-methoxyethyl OH 6-dimethylamino-3-pyridyl S2-methoxyethyl OH 6-(1-pyrrolidinyl)-3-pyridyl S 2-methoxyethyl OH6-piperidino-3-pyridyl S 2-methoxyethyl OH 6-morpholino-3-pyridyl S2-methoxyethyl OH 6-methylthio-3-pyridyl S 2-methoxyethyl OH 2-pyrazinylS 2-methoxyethyl OH 5-methyl-2-pyrazinyl S 2-hydroxyethyl OH 3-pyridyl S2-hydroxyethyl OH 4-pyridyl S 2-hydroxyethyl OH 2-methyl-3-pyridyl S2-hydroxyethyl OH 6-methyl-3-pyridyl S 2-hydroxyethyl OH2-ethyl-3-pyridyl S 2-hydroxyethyl OH 6-ethyl-3-pyridyl S 2-hydroxyethylOH 2-methoxy-3-pyridyl S 2-hydxoxyethyl OH 6-methoxy-3-pyridyl S2-hydroxyethyl OH 6-ethoxy-3-pyridyl S 2-hydroxyethyl OH2-chloro-3-pyridyl S 2-hydroxyethyl OH 6-chloro-3-pyridyl S2-hydroxyethyl OH 5,6-dimethyl-3-pyridyl S 2-hydroxyethyl OH5,6-dimethoxy-3-pyridyl S 2-hydroxyethyl OH 5,6-dichloro-3-pyridyl S2-hydroxyethyl OH 6-dimethylamino-3-pyridyl S 2-hydroxyethyl OH6-(1-pyrrolidinyl)-3-pyridyl S 2-hydroxyethyl OH 6-piperidino-3-pyridylS 2-hydroxyethyl OH 6-morpholino-3-pyridyl S 2-hydroxyethyl OH6-methylthio-3-pyridyl S 2-hydroxyethyl OH 2-pyrazinyl S 2-hydroxyethylOH 5-methyl-2-pyrazinyl NH propyl OH 1-naphthyl NH propyl OH 2-naphthylNH propyl OH 2-pyrrolyl NH propyl OH 3-pyrrolyl NH propyl OH 2-furyl NHpropyl OH 3-furyl NH propyl OH 2-thienyl NH propyl OH 3-thienyl NHpropyl OH 3-pyrazolyl NH propyl OH 4-pyrazolyl NH propyl OH 2-imidazolylNH propyl OH 4-imidazolyl NH propyl OH 2-oxazolyl NH propyl OH4-oxazolyl NH propyl OH 5-oxazolyl NH propyl OH 2-thiazolyl NH propyl OH4-thiazolyl NH propyl OH 5-thiazolyl NH propyl OH 2-pyrimidinyl NHpropyl OH 4-pyrimidinyl NH propyl OH 5-pyrimidinyl NH propyl OH2-indolyl NH propyl OH 3-indolyl NH propyl OH 5-indolyl NH propyl OH6-indolyl NH propyl OH 5-benzimidazolyl NH propyl OH 2-benzofuryl NHpropyl OH 3-indazolyl NH propyl OH 2-benzoxazolyl NH propyl OH4-fluoro-1-naphthyl NH propyl OH 5-chloro-2-thienyl NH propyl OH4-methyl-1-naphthyl NH propyl OH 1-methyl-2-pyrrolyl NH propyl OH2-methyl-3-furyl NH propyl OH 5-methyl-2-thienyl NH propyl OH4-methyl-5-imidazolyl NH propyl OH 1-methyl-3-indolyl NH propyl OH2-methoxy-1-naphthyl NH propyl OH 3-methoxy-2-naphthyl NH propyl OH6-ethoxy-2-naphthyl NH propyl OH 5-methoxy-3-indolyl NH propyl OH1,4-dimethoxy-2-naphthyl NH propyl OH 5,6-dimethoxy-2-indolyl NH propylOH 5-methoxy-1-methyl-2-indolyl NH propyl OCOOMe 1-naphthyl NH propylOCOOMe 2-naphthyl NH propyl OCOOMe 2-pyrrolyl NH propyl OCOOMe3-pyrrolyl NH propyl OCOOMe 2-furyl NH propyl OCOOMe 3-furyl NH propylOCOOMe 2-thienyl NH propyl OCOOMe 3-thienyl NH propyl OCOOMe 3-pyrazolylNH propyl OCOOMe 4-pyrazolyl NH propyl OCOOMe 2-imidazolyl NH propylOCOOMe 4-imidazolyl NH propyl OCOOMe 2-oxazolyl NH propyl OCOOMe4-oxazolyl NH propyl OCOOMe 5-oxazolyl NH propyl OCOOMe 2-thiazolyl NHpropyl OCOOMe 4-thiazolyl NH propyl OCOOMe 5-thiazolyl NH propyl OCOOMe2-pyrimidinyl NH propyl OCOOMe 4-pyrimidinyl NH propyl OCOOMe5-pyrimidinyl NH propyl OCOOMe 2-indolyl NH propyl OCOOMe 3-indolyl NHpropyl OCOOMe 5-indolyl NH propyl OCOOMe 6-indolyl NH propyl OCOOMe5-benzimidazolyl NH propyl OCOOMe 2-benzofuryl NH propyl OCOOMe3-indazolyl NH propyl OCOOMe 2-benzoxazolyl NH propyl OCOOMe4-fluoro-1-naphthyl NH propyl OCOOMe 5-chloro-2-thienyl NH propyl OCOOMe4-methyl-1-naphthyl NH propyl OCOOMe 1-methyl-2-pyrrolyl NH propylOCOOMe 2-methyl-3-furyl NH propyl OCOOMe 5-methyl-2-thienyl NH propylOCOOMe 4-methyl-5-imidazolyl NH propyl OCOOMe 1-methyl-3-indolyl NHpropyl OCOOMe 2-methoxy-1-naphthyl NH propyl OCOOMe 3-methoxy-2-naphthylNH propyl OCOOMe 6-ethoxy-2-naphthyl NH propyl OCOOMe5-methoxy-3-indolyl NH propyl OCOOMe 1,4-dimethoxy-2-naphthyl NH propylOCOOMe 5,6-dimethoxy-2-indolyl NH propyl OCOOMe5-methoxy-1-methyl-2-indolyl NH propyl OCOOEt 1-naphthyl NH propylOCOOEt 2-naphthyl NH propyl OCOOEt 2-pyrrolyl NH propyl OCOOEt3-pyrrolyl NH propyl OCOOEt 2-furyl NH propyl OCOOEt 3-furyl NH propylOCOOEt 2-thienyl NH propyl OCOOEt 3-thienyl NH propyl OCOOEt 3-pyrazolylNH propyl OCOOEt 4-pyrazolyl NH propyl OCOOEt 2-imidazolyl NH propylOCOOEt 4-imidazolyl NH propyl OCOOEt 2-oxazolyl NH propyl OCOOEt4-oxazolyl NH propyl OCOOEt 5-oxazolyl NH propyl OCOOEt 2-thiazolyl NHpropyl OCOOEt 4-thiazolyl NH propyl OCOOEt 5-thiazolyl NH propyl OCOOEt2-pyrimidinyl NH propyl OCOOEt 4-pyrimidinyl NH propyl OCOOEt5-pyrimidinyl NH propyl OCOOEt 2-indolyl NH propyl OCOOEt 3-indolyl NHpropyl OCOOEt 5-indolyl NH propyl OCOOEt 6-indolyl NH propyl OCOOEt5-benzimidazolyl NH propyl OCOOEt 2-benzofuryl NH propyl OCOOEt3-indazolyl NH propyl OCOOEt 2-benzoxazolyl NH propyl OCOOEt4-fluoro-1-naphthyl NH propyl OCOOEt 5-chloro-2-thienyl NH propyl OCOOEt4-methyl-1-naphthyl NH propyl OCOOEt 1-methyl-2-pyrrolyl NH propylOCOOEt 2-methyl-3-furyl NH propyl OCOOEt 5-methyl-2-thienyl NH propylOCOOEt 4-methyl-5-imidazolyl NH propyl OCOOEt 1-methyl-3-indolyl NHpropyl OCOOEt 2-methoxy-1-naphthyl NH propyl OCOOEt 3-methoxy-2-naphthylNH propyl OCOOEt 6-ethoxy-2-naphthyl NH propyl OCOOEt5-methoxy-3-indolyl NH propyl OCOOEt 1,4-dimethoxy-2-naphthyl NH propylOCOOEt 5,6-dimethoxy-2-indolyl NH propyl OCOOEt5-methoxy-1-methyl-2-indolyl NH n-butyl OH 1-naphthyl NH n-butyl OH2-naphthyl NH n-butyl OH 2-pyrrolyl NH n-butyl OH 3-pyrrolyl NH n-butylOH 2-furyl NH n-butyl OH 3-furyl NH n-butyl OH 2-thienyl NH n-butyl OH3-thienyl NH n-butyl OH 3-pyrazolyl NH n-butyl OH 4-pyrazolyl NH n-butylOH 2-imidazolyl NH n-butyl OH 4-imidazolyl NH n-butyl OH 2-oxazolyl NHn-butyl OH 4-oxazolyl NH n-butyl OH 5-oxazolyl NH n-butyl OH 2-thiazolylNH n-butyl OH 4-thiazolyl NH n-butyl OH 5-thiazolyl NH n-butyl OH2-pyrimidinyl NH n-butyl OH 4-pyrimidinyl NH n-butyl OH 5-pyrimidinyl NHn-butyl OH 2-indolyl NH n-butyl OH 3-indolyl NH n-butyl OH 5-indolyl NHn-butyl OH 6-indolyl NH n-butyl OH 5-benzimidazolyl NH n-butyl OH2-benzofuryl NH n-butyl OH 3-indazolyl NH n-butyl OH 2-benzoxazolyl NHn-butyl OH 4-fluoro-1-naphthyl NH n-butyl OH 5-chloro-2-thienyl NHn-butyl OH 4-methyl-1-nahthyl NH n-butyl OH 1-methyl-2-pyrrolyl NHn-butyl OH 2-methyl-3-furyl NH n-butyl OH 5-methyl-2-thienyl NH n-butylOH 4-methyl-5-imidazolyl NH n-butyl OH 1-methyl-3-indolyl NH n-butyl OH2-methoxy-1-naphthyl NH n-butyl OH 3-methoxy-2-naphthyl NH n-butyl OH6-ethoxy-2-naphthyl NH n-butyl OH 5-methoxy-3-indolyl NH n-butyl OH1,4-dimethoxy-2-naphthyl NH n-butyl OH 5,6-dimethoxy-2-indolyl NHn-butyl OH 5-methoxy-1-methyl-2-indolyl NH n-butyl OCOOMe 1-naphthyl NHn-butyl OCOOMe 2-naphthyl NH n-butyl OCOOMe 2-pyrrolyl NH n-butyl OCOOMe3-pyrrolyl NH n-butyl OCOOMe 2-furyl NH n-butyl OCOOMe 3-furyl NHn-butyl OCOOMe 2-thienyl NH n-butyl OCOOMe 3-thienyl NH n-butyl OCOOMe3-pyrazolyl NH n-butyl OCOOMe 4-pyrazolyl NH n-butyl OCOOMe 2-imidazolylNH n-butyl OCOOMe 4-imidazolyl NH n-butyl OCOOMe 2-oxazolyl NH n-butylOCOOMe 4-oxazolyl NH n-butyl OCOOMe 5-oxazolyl NH n-butyl OCOOMe2-thiazolyl NH n-butyl OCOOMe 4-thiazolyl NH n-butyl OCOOMe 5-thiazolylNH n-butyl OCOOMe 2-pyrimidinyl NH n-butyl OCOOMe 4-pyrimidinyl NHn-butyl OCOOMe 5-pyrimidinyl NH n-butyl OCOOMe 2-indolyl NH n-butylOCOOMe 3-indolyl NH n-butyl OCOOMe 5-indolyl NH n-butyl OCOOMe 6-indolylNH n-butyl OCOOMe 5-benzimidazolyl NH n-butyl OCOOMe 2-benzofuryl NHn-butyl OCOOMe 3-indazolyl NH n-butyl OCOOMe 2-benzoxazolyl NH n-butylOCOOMe 4-fluoro-1-naphthyl NH n-butyl OCOOMe 5-chloro-2-thienyl NHn-butyl OCOOMe 4-methyl-1-naphthyl NH n-butyl OCOOMe 1-methyl-2-pyrrolylNH n-butyl OCOOMe 2-methyl-3-furyl NH n-butyl OCOOMe 5-methyl-2-thienylNH n-butyl OCOOMe 4-methyl-5-imidazolyl NH n-butyl OCOOMe1-methyl-3-indolyl NH n-butyl OCOOMe 2-methoxy-1-naphthyl NH n-butylOCOOMe 3-methoxy-2-naphthyl NH n-butyl OCOOMe 6-ethoxy-2-naphthyl NHn-butyl OCOOMe 5-methoxy-3-indolyl NH n-butyl OCOOMe1,4-dimethoxy-2-naphthyl NH n-butyl OCOOMe 5,6-dimethoxy-2-indolyl NHn-butyl OCOOMe 5-methoxy-1-methyl-2-indolyl NH n-butyl OCOOEt 1-naphthylNH n-butyl OCOOEt 2-naphthyl NH n-butyl OCOOEt 2-pyrrolyl NH n-butylOCOOEt 3-pyrrolyl NH n-butyl OCOOEt 2-furyl NH n-butyl OCOOEt 3-furyl NHn-butyl OCOOEt 2-thienyl NH n-butyl OCOOEt 3-thienyl NH n-butyl OCOOEt3-pyrazolyl NH n-butyl OCOOEt 4-pyrazolyl NH n-butyl OCOOEt 2-imidazolylNH n-butyl OCOOEt 4-imidazolyl NH n-butyl OCOOEt 2-oxazolyl NH n-butylOCOOEt 4-oxazolyl NH n-butyl OCOOEt 5-oxazolyl NH n-butyl OCOOEt2-thiazolyl NH n-butyl OCOOEt 4-thiazolyl NH n-butyl OCOOEt 5-thiazolylNH n-butyl OCOOEt 2-pyrimidinyl NH n-butyl OCOOEt 4-pyrimidinyl NHn-butyl OCOOEt 5-pyrimidinyl NH n-butyl OCOOEt 2-indolyl NH n-butylOCOOEt 3-indolyl NH n-butyl OCOOEt 5-indolyl NH n-butyl OCOOEt 6-indolylNH n-butyl OCOOEt 5-benzimidazolyl NH n-butyl OCOOEt 2-benzofuryl NHn-butyl OCOOEt 3-indazolyl NH n-butyl OCOOEt 2-benzoxazolyl NH n-butylOCOOEt 4-fluoro-1-naphthyl NH n-butyl OCOOEt 5-chloro-2-thienyl NHn-butyl OCOOEt 4-methyl-1-naphthyl NH n-butyl OCOOEt 1-methyl-2-pyrrolylNH n-butyl OCOOEt 2-methyl-3-furyl NH n-butyl OCOOEt 5-methyl-2-thienylNH n-butyl OCOOEt 4-methyl-5-imidazolyl NH n-butyl OCOOEt1-methyl-3-indolyl NH n-butyl OCOOEt 2-methoxy-1-naphthyl NH n-butylOCOOEt 3-methoxy-2-naphthyl NH n-butyl OCOOEt 6-ethoxy-2-naphthyl NHn-butyl OCOOEt 5-methoxy-3-indolyl NH n-butyl OCOOEt1,4-dimethoxy-2-naphthyl NH n-butyl OCOOEt 5,6-dimethoxy-2-indolyl NHn-butyl OCOOEt 5-methoxy-1-methyl-2-indolyl NH n-pentyl OH 1-naphthyl NHn-pentyl OH 2-naphthyl NH n-pentyl OH 2-pyrrolyl NH n-pentyl OH3-pyrrolyl NH n-pentyl OH 2-furyl NH n-pentyl OH 3-furyl NH n-pentyl OH2-thienyl NH n-pentyl OH 3-thienyl NH n-pentyl OH 3-pyrazolyl NHn-pentyl OH 4-pyrazolyl NH n-pentyl OH 2-imidazolyl NH n-pentyl OH4-imidazolyl NH n-pentyl OH 2-oxazolyl NH n-pentyl OH 4-oxazolyl NHn-pentyl OH 5-oxazolyl NH n-pentyl OH 2-thiazolyl NH n-pentyl OH4-thiazolyl NH n-pentyl OH 5-thiazolyl NH n-pentyl OH 2-pyrimidinyl NHn-pentyl OH 4-pyrimidinyl NH n-pentyl OH 5-pyrimidinyl NH n-pentyl OH2-indolyl NH n-pentyl OH 3-indolyl NH n-pentyl OH 5-indolyl NH n-pentylOH 6-indolyl NH n-pentyl OH 5-benzimidazolyl NH n-pentyl OH 2-benzofurylNH n-pentyl OH 3-indazolyl NH n-pentyl OH 2-benzoxazolyl NH n-pentyl OH4-fluoro-1-naphthyl NH n-pentyl OH 5-chloro-2-thienyl NH n-pentyl OH4-methyl-1-naphthyl NH n-pentyl OH 1-methyl-2-pyrrolyl NH n-pentyl OH2-methyl-3-furyl NH n-pentyl OH 5-methyl-2-thienyl NH n-pentyl OH4-methyl-5-imidazolyl NH n-pentyl OH 1-methyl-3-indolyl NH n-pentyl OH2-methoxy-1-naphthyl NH n-pentyl OH 3-methoxy-2-naphthyl NH n-pentyl OH6-ethoxy-2-naphthyl NH n-pentyl OH 5-methoxy-3-indolyl NH n-pentyl OH1,4-dimethoxy-2-naphthyl NH n-pentyl OH 5,6-dimethoxy-2-indolyl NHn-pentyl OH 5-methoxy-1-methyl-2-indolyl NH n-pentyl OCOOMe 1-naphthylNH n-pentyl OCOOMe 2-naphthyl NH n-pentyl OCOOMe 2-pyrrolyl NH n-pentylOCOOMe 3-pyrrolyl NH n-pentyl OCOOMe 2-furyl NH n-pentyl OCOOMe 3-furylNH n-pentyl OCOOMe 2-thienyl NH n-pentyl OCOOMe 3-thienyl NH n-pentylOCOOMe 3-pyrazolyl NH n-pentyl OCOOMe 4-pyrazolyl NH n-pentyl OCOOMe2-imidazolyl NH n-pentyl OCOOMe 4-imidazolyl NH n-pentyl OCOOMe2-oxazolyl NH n-pentyl OCOOMe 4-oxazolyl NH n-pentyl OCOOMe 5-oxazolylNH n-pentyl OCOOMe 2-thiazolyl NH n-pentyl OCOOMe 4-thiazolyl NHn-pentyl OCOOMe 5-thiazolyl NH n-pentyl OCOOMe 2-pyrimidinyl NH n-pentylOCOOMe 4-pyrimidinyl NH n-pentyl OCOOMe 5-pyrimidinyl NH n-pentyl OCOOMe2-indolyl NH n-pentyl OCOOMe 3-indolyl NH n-pentyl OCOOMe 5-indolyl NHn-pentyl OCOOMe 6-indolyl NH n-pentyl OCOOMe 5-benzimidazolyl NHn-pentyl OCOOMe 2-benzofuryl NH n-pentyl OCOOMe 3-indazolyl NH n-pentylOCOOMe 2-benzoxazolyl NH n-pentyl OCOOMe 4-fluoro-1-naphthyl NH n-pentylOCOOMe 5-chloro-2-thienyl NH n-pentyl OCOOMe 4-methyl-1-naphthyl NHn-pentyl OCOOMe 1-methyl-2-pyrrolyl NH n-pentyl OCOOMe 2-methyl-3-furylNH n-pentyl OCOOMe 5-methyl-2-thienyl NH n-pentyl OCOOMe4-methyl-5-imidazolyl NH n-pentyl OCOOMe 1-methyl-3-indolyl NH n-pentylOCOOMe 2-methoxy-1-naphthyl NH n-pentyl OCOOMe 3-methoxy-2-naphthyl NHn-pentyl OCOOMe 6-ethoxy-2-naphthyl NH n-pentyl OCOOMe5-methoxy-3-indolyl NH n-pentyl OCOOMe 1,4-dimethoxy-2-naphthyl NHn-pentyl OCOOMe 5,6-dimethoxy-2-indolyl NH n-pentyl OCOOMe5-methoxy-1-methyl-2-indolyl NH n-pentyl OCOOEt 1-naphthyl NH n-pentylOCOOEt 2-naphthyl NH n-pentyl OCOOEt 2-pyrrolyl NH n-pentyl OCOOEt3-pyrrolyl NH n-pentyl OCOOEt 2-furyl NH n-pentyl OCOOEt 3-furyl NHn-pentyl OCOOEt 2-thienyl NH n-pentyl OCOOEt 3-thienyl NH n-pentylOCOOEt 3-pyrazolyl NH n-pentyl OCOOEt 4-pyrazolyl NH n-pentyl OCOOEt2-imidazolyl NH n-pentyl OCOOEt 4-imidazolyl NH n-pentyl OCOOEt2-oxazolyl NH n-pentyl OCOOEt 4-oxazolyl NH n-pentyl OCOOEt 5-oxazolylNH n-pentyl OCOOEt 2-thiazolyl NH n-pentyl OCOOEt 4-thiazolyl NHn-pentyl OCOOEt 5-thiazolyl NH n-pentyl OCOOEt 2-pyrimidinyl NH n-pentylOCOOEt 4-pyrimidinyl NH n-pentyl OCOOEt 5-pyrimidinyl NH n-pentyl OCOOEt2-indolyl NH n-pentyl OCOOEt 3-indolyl NH n-pentyl OCOOEt 5-indolyl NHn-pentyl OCOOEt 6-indolyl NH n-pentyl OCOOEt 5-benzimidazolyl NHn-pentyl OCOOEt 2-benzofuryl NH n-pentyl OCOOEt 3-indazolyl NH n-pentylOCOOEt 2-benzoxazolyl NH n-pentyl OCOOEt 4-fluoro-1-naphthyl NH n-pentylOCOOEt 5-chloro-2-thienyl NH n-pentyl OCOOEt 4-methyl-1-naphthyl NHn-pentyl OCOOEt 1-methyl-2-pyrrolyl NH n-pentyl OCOOEt 2-methyl-3-furylNH n-pentyl OCOOEt 5-methyl-2-thienyl NH n-pentyl OCOOEt4-methyl-5-imidazolyl NH n-pentyl OCOOEt 1-methyl-3-indolyl NH n-pentylOCOOEt 2-methoxy-1-naphthyl NH n-pentyl OCOOEt 3-methoxy-2-naphthyl NHn-pentyl OCOOEt 6-ethoxy-2-naphthyl NH n-pentyl OCOOEt5-methoxy-3-indolyl NH n-pentyl OCOOEt 1,4-dimethoxy-2-naphthyl NHn-pentyl OCOOEt 5,6-dimethoxy-2-indolyl NH n-pentyl OCOOEt5-methoxy-1-methyl-2-indolyl O propyl OH 1-naphthyl O propyl OH2-naphthyl O propyl OH 2-pyrrolyl O propyl OH 3-pyrrolyl O propyl OH2-furyl O propyl OH 3-furyl O propyl OH 2-thienyl O propyl OH 3-thienylO propyl OH 3-pyrazolyl O propyl OH 4-pyrazolyl O propyl OH 2-imidazolylO propyl OH 4-imidazolyl O propyl OH 2-oxazolyl O propyl OH 4-oxazolyl Opropyl OH 5-oxazolyl O propyl OH 2-thiazolyl O propyl OH 4-thiazolyl Opropyl OH 5-thiazolyl O propyl OH 2-pyrimidinyl O propyl OH4-pyrimidinyl O propyl OH 5-pyrimidinyl O propyl OH 2-indolyl O propylOH 3-indolyl O propyl OH 5-indolyl O propyl OH 6-indolyl O propyl OH5-benzimidazolyl O propyl OH 2-benzofuryl O propyl OH 3-indazolyl Opropyl OH 2-benzoxazolyl O propyl OH 4-fluoro-1-naphthyl O propyl OH5-chloro-2-thienyl O propyl OH 4-methyl-1-naphthyl O propyl OH1-methyl-2-pyrrolyl O propyl OH 2-methyl-3-furyl O propyl OH5-methyl-2-thienyl O propyl OH 4-methyl-5-imidazolyl O propyl OH1-methyl-3-indolyl O propyl OH 2-methoxy-1-naphthyl O propyl OH3-methoxy-2-naphthyl O propyl OH 6-ethoxy-2-naphthyl O propyl OH5-methoxy-3-indolyl O propyl OH 1,4-dimethoxy-2-naphthyl O propyl OH5,6-dimethoxy-2-indolyl O propyl OH 5-methoxy-1-methyl-2-indolyl Opropyl OCOOMe 1-naphthyl O propyl OCOOMe 2-naphthyl O propyl OCOOMe2-pyrrolyl O propyl OCOOMe 3-pyrrolyl O propyl OCOOMe 2-furyl O propylOCOOMe 3-furyl O propyl OCOOMe 2-thienyl O propyl OCOOMe 3-thienyl Opropyl OCOOMe 3-pyrazolyl O propyl OCOOMe 4-pyrazolyl O propyl OCOOMe2-imidazolyl O propyl OCOOMe 4-imidazolyl O propyl OCOOMe 2-oxazolyl Opropyl OCOOMe 4-oxazolyl O propyl OCOOMe 5-oxazolyl O propyl OCOOMe2-thiazolyl O propyl OCOOMe 4-thiazolyl O propyl OCOOMe 5-thiazolyl Opropyl OCOOMe 2-pyrimidinyl O propyl OCOOMe 4-pyrimidinyl O propylOCOOMe 5-pyrimidinyl O propyl OCOOMe 2-indolyl O propyl OCOOMe 3-indolylO propyl OCOOMe 5-indolyl O propyl OCOOMe 6-indolyl O propyl OCOOMe5-benzimidazolyl O propyl OCOOMe 2-benzofuryl O propyl OCOOMe3-indazolyl O propyl OCOOMe 2-benzoxazolyl O propyl OCOOMe4-fluoro-1-naphthyl O propyl OCOOMe 5-chloro-2-thienyl O propyl OCOOMe4-methyl-1-naphthyl O propyl OCOOMe 1-methyl-2-pyrrolyl O propyl OCOOMe2-methyl-3-furyl O propyl OCOOMe 5-methyl-2-thienyl O propyl OCOOMe4-methyl-5-imidazolyl O propyl OCOOMe 1-methyl-3-indolyl O propyl OCOOMe2-methoxy-1-naphthyl O propyl OCOOMe 3-methoxy-2-naphthyl O propylOCOOMe 6-ethoxy-2-naphthyl O propyl OCOOMe 5-methoxy-3-indolyl O propylOCOOMe 1,4-dimethoxy-2-naphthyl O propyl OCOOMe 5,6-dimethoxy-2-indolylO propyl OCOOMe 5-methoxy-1-methyl-2-indolyl O propyl OCOOEt 1-naphthylO propyl OCOOEt 2-naphthyl O propyl OCOOEt 2-pyrrolyl O propyl OCOOEt3-pyrrolyl O propyl OCOOEt 2-furyl O propyl OCOOEt 3-furyl O propylOCOOEt 2-thienyl O propyl OCOOEt 3-thienyl O propyl OCOOEt 3-pyrazolyl Opropyl OCOOEt 4-pyrazolyl O propyl OCOOEt 2-imidazolyl O propyl OCOOEt4-imidazolyl O propyl OCOOEt 2-oxazolyl O propyl OCOOEt 4-oxazolyl Opropyl OCOOEt 5-oxazolyl O propyl OCOOEt 2-thiazolyl O propyl OCOOEt4-thiazolyl O propyl OCOOEt 5-thiazolyl O propyl OCOOEt 2-pyrimidinyl Opropyl OCOOEt 4-pyrimidinyl O propyl OCOOEt 5-pyrimidinyl O propylOCOOEt 2-indolyl O propyl OCOOEt 3-indolyl O propyl OCOOEt 5-indolyl Opropyl OCOOEt 6-indolyl O propyl OCOOEt 5-benzimidazolyl O propyl OCOOEt2-benzofuryl O propyl OCOOEt 3-indazolyl O propyl OCOOEt 2-benzoxazolylO propyl OCOOEt 4-fluoro-1-naphthyl O propyl OCOOEt 5-chloro-2-thienyl Opropyl OCOOEt 4-methyl-1-naphthyl O propyl OCOOEt 1-methyl-2-pyrrolyl Opropyl OCOOEt 2-methyl-3-furyl O propyl OCOOEt 5-methyl-2-thienyl Opropyl OCOOEt 4-methyl-5-imidazolyl O propyl OCOOEt 1-methyl-3-indolyl Opropyl OCOOEt 2-methoxy-1-naphthyl O propyl OCOOEt 3-methoxy-2-naphthylO propyl OCOOEt 6-ethoxy-2-naphthyl O propyl OCOOEt 5-methoxy-3-indolylO propyl OCOOEt 1,4-dimethoxy-2-naphthyl O propyl OCOOEt5,6-dimethoxy-2-indolyl O propyl OCOOEt 5-methoxy-1-methyl-2-indolyl On-butyl OH 1-naphthyl O n-butyl OH 2-naphthyl O n-butyl OH 2-pyrrolyl On-butyl OH 3-pyrrolyl O n-butyl OH 2-furyl O n-butyl OH 3-furyl On-butyl OH 2-thienyl O n-butyl OH 3-thienyl O n-butyl OH 3-pyrazolyl On-butyl OH 4-pyrazolyl O n-butyl OH 2-imidazolyl O n-butyl OH4-imidazolyl O n-butyl OH 2-oxazolyl O n-butyl OH 4-oxazolyl O n-butylOH 5-oxazolyl O n-butyl OH 2-thiazolyl O n-butyl OH 4-thiazolyl On-butyl OH 5-thiazolyl O n-butyl OH 2-pyrimidinyl O n-butyl OH4-pyrimidinyl O n-butyl OH 5-pyrimidinyl O n-butyl OH 2-indolyl On-butyl OH 3-indolyl O n-butyl OH 5-indolyl O n-butyl OH 6-indolyl On-butyl OH 5-benzimidazolyl O n-butyl OH 2-benzofuryl O n-butyl OH3-indazolyl O n-butyl OH 2-benzoxazolyl O n-butyl OH 4-fluoro-1-naphthylO n-butyl OH 5-chloro-2-thienyl O n-butyl OH 4-methyl-1-naphthyl On-butyl OH 1-methyl-2-pyrrolyl O n-butyl OH 2-methyl-3-furyl O n-butylOH 5-methyl-2-thienyl O n-butyl OH 4-methyl-5-imidazolyl O n-butyl OH1-methyl-3-indolyl O n-butyl OH 2-methoxy-1-naphthyl O n-butyl OH3-methoxy-2-naphthyl O n-butyl OH 6-ethoxy-2-naphthyl O n-butyl OH5-methoxy-3-indolyl O n-butyl OH 1,4-dimethoxy-2-naphthyl O n-butyl OH5,6-dimethoxy-2-indolyl O n-butyl OH 5-methoxy-1-methyl-2-indolyl On-butyl OCOOMe 1-naphthyl O n-butyl OCOOMe 2-naphthyl O n-butyl OCOOMe2-pyrrolyl O n-butyl OCOOMe 3-pyrrolyl O n-butyl OCOOMe 2-furyl On-butyl OCOOMe 3-furyl O n-butyl OCOOMe 2-thienyl O n-butyl OCOOMe3-thienyl O n-butyl OCOOMe 3-pyrazolyl O n-butyl OCOOMe 4-pyrazolyl On-butyl OCOOMe 2-imidazolyl O n-butyl OCOOMe 4-imidazolyl O n-butylOCOOMe 2-oxazolyl O n-butyl OCOOMe 4-oxazolyl O n-butyl OCOOMe5-oxazolyl O n-butyl OCOOMe 2-thiazolyl O n-butyl OCOOMe 4-thiazolyl On-butyl OCOOMe 5-thiazolyl O n-butyl OCOOMe 2-pyrimidinyl O n-butylOCOOMe 4-pyrimidinyl O n-butyl OCOOMe 5-pyrimidinyl O n-butyl OCOOMe2-indolyl O n-butyl OCOOMe 3-indolyl O n-butyl OCOOMe 5-indolyl On-butyl OCOOMe 6-indolyl O n-butyl OCOOMe 5-benzimidazolyl O n-butylOCOOMe 2-benzofuryl O n-butyl OCOOMe 3-indazolyl O n-butyl OCOOMe2-benzoxazolyl O n-butyl OCOOMe 4-fluoro-1-naphthyl O n-butyl OCOOMe5-chloro-2-thienyl O n-butyl OCOOMe 4-methyl-1-naphthyl O n-butyl OCOOMe1-methyl-2-pyrrolyl O n-butyl OCOOMe 2-methyl-3-furyl O n-butyl OCOOMe5-methyl-2-thienyl O n-butyl OCOOMe 4-methyl-5-imidazolyl O n-butylOCOOMe 1-methyl-3-indolyl O n-butyl OCOOMe 2-methoxy-1-naphthyl On-butyl OCOOMe 3-methoxy-2-naphthyl O n-butyl OCOOMe 6-ethoxy-2-naphthylO n-butyl OCOOMe 5-methoxy-3-indolyl O n-butyl OCOOMe1,4-dimethoxy-2-naphthyl O n-butyl OCOOMe 5,6-dimethoxy-2-indolyl On-butyl OCOOMe 5-methoxy-1-methyl-2-indolyl O n-butyl OCOOEt 1-naphthylO n-butyl OCOOEt 2-naphthyl O n-butyl OCOOEt 2-pyrrolyl O n-butyl OCOOEt3-pyrrolyl O n-butyl OCOOEt 2-furyl O n-butyl OCOOEt 3-furyl O n-butylOCOOEt 2-thienyl O n-butyl OCOOEt 3-thienyl O n-butyl OCOOEt 3-pyrazolylO n-butyl OCOOEt 4-pyrazolyl O n-butyl OCOOEt 2-imidazolyl O n-butylOCOOEt 4-imidazolyl O n-butyl OCOOEt 2-oxazolyl O n-butyl OCOOEt4-oxazolyl O n-butyl OCOOEt 5-oxazolyl O n-butyl OCOOEt 2-thiazolyl On-butyl OCOOEt 4-thiazolyl O n-butyl OCOOEt 5-thiazolyl O n-butyl OCOOEt2-pyrimidinyl O n-butyl OCOOEt 4-pyrimidinyl O n-butyl OCOOEt5-pyrimidinyl O n-butyl OCOOEt 2-indolyl O n-butyl OCOOEt 3-indolyl On-butyl OCOOEt 5-indolyl O n-butyl OCOOEt 6-indolyl O n-butyl OCOOEt5-benzimidazolyl O n-butyl OCOOEt 2-benzofuryl O n-butyl OCOOEt3-indazolyl O n-butyl OCOOEt 2-benzoxazolyl O n-butyl OCOOEt4-fluoro-1-naphthyl O n-butyl OCOOEt 5-chloro-2-thienyl O n-butyl OCOOEt4-methyl-1-naphthyl O n-butyl OCOOEt 1-methyl-2-pyrrolyl O n-butylOCOOEt 2-methyl-3-furyl O n-butyl OCOOEt 5-methyl-2-thienyl O n-butylOCOOEt 4-methyl-5-imidazolyl O n-butyl OCOOEt 1-methyl-3-indolyl On-butyl OCOOEt 2-methoxy-1-naphthyl O n-butyl OCOOEt3-methoxy-2-naphthyl O n-butyl OCOOEt 6-ethoxy-2-naphthyl O n-butylOCOOEt 5-methoxy-3-indolyl O n-butyl OCOOEt 1,4-dimethoxy-2-naphthyl On-butyl OCOOEt 5,6-dimethoxy-2-indolyl O n-butyl OCOOEt5-methoxy-1-methyl-2-indolyl O n-pentyl OH 1-naphthyl O n-pentyl OH2-naphthyl O n-pentyl OH 2-pyrrolyl O n-pentyl OH 3-pyrrolyl O n-pentylOH 2-furyl O n-pentyl OH 3-furyl O n-pentyl OH 2-thienyl O n-pentyl OH3-thienyl O n-pentyl OH 3-pyrazolyl O n-pentyl OH 4-pyrazolyl O n-pentylOH 2-imidazolyl O n-pentyl OH 4-imidazolyl O n-pentyl OH 2-oxazolyl On-pentyl OH 4-oxazolyl O n-pentyl OH 5-oxazolyl O n-pentyl OH2-thiazolyl O n-pentyl OH 4-thiazolyl O n-pentyl OH 5-thiazolyl On-pentyl OH 2-pyrimidinyl O n-pentyl OH 4-pyrimidinyl O n-pentyl OH5-pyrimidinyl O n-pentyl OH 2-indolyl O n-pentyl OH 3-indolyl O n-pentylOH 5-indolyl O n-pentyl OH 6-indolyl O n-pentyl OH 5-benzimidazolyl On-pentyl OH 2-benzofuryl O n-pentyl OH 3-indazolyl O n-pentyl OH2-benzoxazolyl O n-pentyl OH 4-fluoro-1-naphthyl O n-pentyl OH5-chloro-2-thienyl O n-pentyl OH 4-methyl-1-naphthyl O n-pentyl OH1-methyl-2-pyrrolyl O n-pentyl OH 2-methyl-3-furyl O n-pentyl OH5-methyl-2-thienyl O n-pentyl OH 4-methyl-5-imidazolyl O n-pentyl OH1-methyl-3-indolyl O n-pentyl OH 2-methoxy-1-naphthyl O n-pentyl OH3-methoxy-2-naphthyl O n-pentyl OH 6-ethoxy-2-naphthyl O n-pentyl OH5-methoxy-3-indolyl O n-pentyl OH 1,4-dimethoxy-2-naphthyl O n-pentyl OH5,6-dimethoxy-2-indolyl O n-pentyl OH 5-methoxy-1-methyl-2-indolyl On-pentyl OCOOMe 1-naphthyl O n-pentyl OCOOMe 2-naphthyl O n-pentylOCOOMe 2-pyrrolyl O n-pentyl OCOOMe 3-pyrrolyl O n-pentyl OCOOMe 2-furylO n-pentyl OCOOMe 3-furyl O n-pentyl OCOOMe 2-thienyl O n-pentyl OCOOMe3-thienyl O n-pentyl OCOOMe 3-pyrazolyl O n-pentyl OCOOMe 4-pyrazolyl On-pentyl OCOOMe 2-imidazolyl O n-pentyl OCOOMe 4-imidazolyl O n-pentylOCOOMe 2-oxazolyl O n-pentyl OCOOMe 4-oxazolyl O n-pentyl OCOOMe5-oxazolyl O n-pentyl OCOOMe 2-thiazolyl O n-pentyl OCOOMe 4-thiazolyl On-pentyl OCOOMe 5-thiazolyl O n-pentyl OCOOMe 2-pyrimidinyl O n-pentylOCOOMe 4-pyrimidinyl O n-pentyl OCOOMe 5-pyrimidinyl O n-pentyl OCOOMe2-indolyl O n-pentyl OCOOMe 3-indolyl O n-pentyl OCOOMe 5-indolyl On-pentyl OCOOMe 6-indolyl O n-pentyl OCOOMe 5-benzimidazolyl O n-pentylOCOOMe 2-benzofuryl O n-pentyl OCOOMe 3-indazolyl O n-pentyl OCOOMe2-benzoxazolyl O n-pentyl OCOOMe 4-fluoro-1-naphthyl O n-pentyl OCOOMe5-chloro-2-thienyl O n-pentyl OCOOMe 4-methyl-1-naphthyl O n-pentylOCOOMe 1-methyl-2-pyrrolyl O n-pentyl OCOOMe 2-methyl-3-furyl O n-pentylOCOOMe 5-methyl-2-thienyl O n-pentyl OCOOMe 4-methyl-5-imidazolyl On-pentyl OCOOMe 1-methyl-3-indolyl O n-pentyl OCOOMe2-methoxy-1-naphthyl O n-pentyl OCOOMe 3-methoxy-2-naphthyl O n-pentylOCOOMe 6-ethoxy-2-naphthyl O n-pentyl OCOOMe 5-methoxy-3-indolyl On-pentyl OCOOMe 1,4-dimethoxy-2-naphthyl O n-pentyl OCOOMe5,6-dimethoxy-2-indolyl O n-pentyl OCOOMe 5-methoxy-1-methyl-2-indolyl On-pentyl OCOOEt 1-naphthyl O n-pentyl OCOOEt 2-naphthyl O n-pentylOCOOEt 2-pyrrolyl O n-pentyl OCOOEt 3-pyrrolyl O n-pentyl OCOOEt 2-furylO n-pentyl OCOOEt 3-furyl O n-pentyl OCOOEt 2-thienyl O n-pentyl OCOOEt3-thienyl O n-pentyl OCOOEt 3-pyrazolyl O n-pentyl OCOOEt 4-pyrazolyl On-pentyl OCOOEt 2-imidazolyl O n-pentyl OCOOEt 4-imidazolyl O n-pentylOCOOEt 2-oxazolyl O n-pentyl OCOOEt 4-oxazolyl O n-pentyl OCOOEt5-oxazolyl O n-pentyl OCOOEt 2-thiazolyl O n-pentyl OCOOEt 4-thiazolyl On-pentyl OCOOEt 5-thiazolyl O n-pentyl OCOOEt 2-pyrimidinyl O n-pentylOCOOEt 4-pyrimidinyl O n-pentyl OCOOEt 5-pyrimidinyl O n-pentyl OCOOEt2-indolyl O n-pentyl OCOOEt 3-indolyl O n-pentyl OCOOEt 5-indolyl On-pentyl OCOOEt 6-indolyl O n-pentyl OCOOEt 5-benzimidazolyl O n-pentylOCOOEt 2-benzofuryl O n-pentyl OCOOEt 3-indazolyl O n-pentyl OCOOEt2-benzoxazolyl O n-pentyl OCOOEt 4-fluoro-1-naphthyl O n-pentyl OCOOEt5-chloro-2-thienyl O n-pentyl OCOOEt 4-methyl-1-naphthyl O n-pentylOCOOEt 1-methyl-2-pyrrolyl O n-pentyl OCOOEt 2-methyl-3-furyl O n-pentylOCOOEt 5-methyl-2-thienyl O n-pentyl OCOOEt 4-methyl-5-imidazolyl On-pentyl OCOOEt 1-methyl-3-indolyl O n-pentyl OCOOEt2-methoxy-1-naphthyl O n-pentyl OCOOEt 3-methoxy-2-naphthyl O n-pentylOCOOEt 6-ethoxy-2-naphthyl O n-pentyl OCOOEt 5-methoxy-3-indolyl On-pentyl OCOOEt 1,4-dimethoxy-2-naphthyl O n-pentyl OCOOEt5,6-dimethoxy-2-indolyl O n-pentyl OCOOEt 5-methoxy-1-methyl-2-indolyl Spropyl OH 1-naphthyl S propyl OH 2-naphthyl S propyl OH 2-pyrrolyl Spropyl OH 3-pyrrolyl S propyl OH 2-furyl S propyl OH 3-furyl S propyl OH2-thienyl S propyl OH 3-thienyl S propyl OH 3-pyrazolyl S propyl OH4-pyrazolyl S propyl OH 2-imidazolyl S propyl OH 4-imidazolyl S propylOH 2-oxazolyl S propyl OH 4-oxazolyl S propyl OH 5-oxazolyl S propyl OH2-thiazolyl S propyl OH 4-thiazolyl S propyl OH 5-thiazolyl S propyl OH2-pyrimidinyl S propyl OH 4-pyrimidinyl S propyl OH 5-pyrimidinyl Spropyl OH 2-indolyl S propyl OH 3-indolyl S propyl OH 5-indolyl S propylOH 6-indolyl S propyl OH 5-benzimidazolyl S propyl OH 2-benzofuryl Spropyl OH 3-indazolyl S propyl OH 2-benzoxazolyl S propyl OH4-fluoro-1-naphthyl S propyl OH 5-chloro-2-thienyl S propyl OH4-methyl-1-naphthyl S propyl OH 1-methyl-2-pyrrolyl S propyl OH2-methyl-3-furyl S propyl OH 5-methyl-2-thienyl S propyl OH4-methyl-5-imidazolyl S propyl OH 1-methyl-3-indolyl S propyl OH2-methoxy-1-naphthyl S propyl OH 3-methoxy-2-naphthyl S propyl OH6-ethoxy-2-naphthyl S propyl OH 5-methoxy-3-indolyl S propyl OH1,4-dimethoxy-2-naphthyl S propyl OH 5,6-dimethoxy-2-indolyl S propyl OH5-methoxy-1-methyl-2-indolyl S propyl OCOOMe 1-naphthyl S propyl OCOOMe2-naphthyl S propyl OCOOMe 2-pyrrolyl S propyl OCOOMe 3-pyrrolyl Spropyl OCOOMe 2-furyl S propyl OCOOMe 3-furyl S propyl OCOOMe 2-thienylS propyl OCOOMe 3-thienyl S propyl OCOOMe 3-pyrazolyl S propyl OCOOMe4-pyrazolyl S propyl OCOOMe 2-imidazolyl S propyl OCOOMe 4-imidazolyl Spropyl OCOOMe 2-oxazolyl S propyl OCOOMe 4-oxazolyl S propyl OCOOMe5-oxazolyl S propyl OCOOMe 2-thiazolyl S propyl OCOOMe 4-thiazolyl Spropyl OCOOMe 5-thiazolyl S propyl OCOOMe 2-pyrimidinyl S propyl OCOOMe4-pyrimidinyl S propyl OCOOMe 5-pyrimidinyl S propyl OCOOMe 2-indolyl Spropyl OCOOMe 3-indolyl S propyl OCOOMe 5-indolyl S propyl OCOOMe6-indolyl S propyl OCOOMe 5-benzimidazolyl S propyl OCOOMe 2-benzofurylS propyl OCOOMe 3-indazolyl S propyl OCOOMe 2-benzoxazolyl S propylOCOOMe 4-fluoro-1-naphthyl S propyl OCOOMe 5-chloro-2-thienyl S propylOCOOMe 4-methyl-1-naphthyl S propyl OCOOMe 1-methyl-2-pyrrolyl S propylOCOOMe 2-methyl-3-furyl S propyl OCOOMe 5-methyl-2-thienyl S propylOCOOMe 4-methyl-5-imidazolyl S propyl OCOOMe 1-methyl-3-indolyl S propylOCOOMe 2-methoxy-1-naphthyl S propyl OCOOMe 3-methoxy-2-naphthyl Spropyl OCOOMe 6-ethoxy-2-naphthyl S propyl OCOOMe 5-methoxy-3-indolyl Spropyl OCOOMe 1,4-dimethoxy-2-naphthyl S propyl OCOOMe5,6-dimethoxy-2-indolyl S propyl OCOOMe 5-methoxy-1-methyl-2-indolyl Spropyl OCOOEt 1-naphthyl S propyl OCOOEt 2-naphthyl S propyl OCOOEt2-pyrrolyl S propyl OCOOEt 3-pyrrolyl S propyl OCOOEt 2-furyl S propylOCOOEt 3-furyl S propyl OCOOEt 2-thienyl S propyl OCOOEt 3-thienyl Spropyl OCOOEt 3-pyrazolyl S propyl OCOOEt 4-pyrazolyl S propyl OCOOEt2-imidazolyl S propyl OCOOEt 4-imidazolyl S propyl OCOOEt 2-oxazolyl Spropyl OCOOEt 4-oxazolyl S propyl OCOOEt 5-oxazolyl S propyl OCOOEt2-thiazolyl S propyl OCOOEt 4-thiazolyl S propyl OCOOEt 5-thiazolyl Spropyl OCOOEt 2-pyrimidinyl S propyl OCOOEt 4-pyrimidinyl S propylOCOOEt 5-pyrimidinyl S propyl OCOOEt 2-indolyl S propyl OCOOEt 3-indolylS propyl OCOOEt 5-indolyl S propyl OCOOEt 6-indolyl S propyl OCOOEt5-benzimidazolyl S propyl OCOOEt 2-benzofuryl S propyl OCOOEt3-indazolyl S propyl OCOOEt 2-benzoxazolyl S propyl OCOOEt4-fluoro-1-naphthyl S propyl OCOOEt 5-chloro-2-thienyl S propyl OCOOEt4-methyl-1-naphthyl S propyl OCOOEt 1-methyl-2-pyrrolyl S propyl OCOOEt2-methyl-3-furyl S propyl OCOOEt 5-methyl-2-thienyl S propyl OCOOEt4-methyl-5-imidazolyl S propyl OCOOEt 1-methyl-3-indolyl S propyl OCOOEt2-methoxy-1-naphthyl S propyl OCOOEt 3-methoxy-2-naphthyl S propylOCOOEt 6-ethoxy-2-naphthyl S propyl OCOOEt 5-methoxy-3-indolyl S propylOCOOEt 1,4-dimethoxy-2-naphthyl S propyl OCOOEt 5,6-dimethoxy-2-indolylS propyl OCOOEt 5-methoxy-1-methyl-2-indolyl S n-butyl OH 1-naphthyl Sn-butyl OH 2-naphthyl S n-butyl OH 2-pyrrolyl S n-butyl OH 3-pyrrolyl Sn-butyl OH 2-furyl S n-butyl OH 3-furyl S n-butyl OH 2-thienyl S n-butylOH 3-thienyl S n-butyl OH 3-pyrazolyl S n-butyl OH 4-pyrazolyl S n-butylOH 2-imidazolyl S n-butyl OH 4-imidazolyl S n-butyl OH 2-oxazolyl Sn-butyl OH 4-oxazolyl S n-butyl OH 5-oxazolyl S n-butyl OH 2-thiazolyl Sn-butyl OH 4-thiazolyl S n-butyl OH 5-thiazolyl S n-butyl OH2-pyrimidinyl S n-butyl OH 4-pyrimidinyl S n-butyl OH 5-pyrimidinyl Sn-butyl OH 2-indolyl S n-butyl OH 3-indolyl S n-butyl OH 5-indolyl Sn-butyl OH 6-indolyl S n-butyl OH 5-benzimidazolyl S n-butyl OH2-benzofuryl S n-butyl OH 3-indazolyl S n-butyl OH 2-benzoxazolyl Sn-butyl OH 4-fluoro-1-naphthyl S n-butyl OH 5-chloro-2-thienyl S n-butylOH 4-methyl-1-naphthyl S n-butyl OH 1-methyl-2-pyrrolyl S n-butyl OH2-methyl-3-furyl S n-butyl OH 5-methyl-2-thienyl S n-butyl OH4-methyl-5-imidazolyl S n-butyl OH 1-methyl-3-indolyl S n-butyl OH2-methoxy-1-naphthyl S n-butyl OH 3-methoxy-2-naphthyl S n-butyl OH6-ethoxy-2-naphthyl S n-butyl OH 5-methoxy-3-indolyl S n-butyl OH1,4-dimethoxy-2-naphthyl S n-butyl OH 5,6-dimethoxy-2-indolyl S n-butylOH 5-methoxy-1-methyl-2-indolyl S n-butyl OCOOMe 1-naphthyl S n-butylOCOOMe 2-naphthyl S n-butyl OCOOMe 2-pyrrolyl S n-butyl OCOOMe3-pyrrolyl S n-butyl OCOOMe 2-furyl S n-butyl OCOOMe 3-furyl S n-butylOCOOMe 2-thienyl S n-butyl OCOOMe 3-thienyl S n-butyl OCOOMe 3-pyrazolylS n-butyl OCOOMe 4-pyrazolyl S n-butyl OCOOMe 2-imidazolyl S n-butylOCOOMe 4-imidazolyl S n-butyl OCOOMe 2-oxazolyl S n-butyl OCOOMe4-oxazolyl S n-butyl OCOOMe 5-oxazolyl S n-butyl OCOOMe 2-thiazolyl Sn-butyl OCOOMe 4-thiazolyl S n-butyl OCOOMe 5-thiazolyl S n-butyl OCOOMe2-pyrimidinyl S n-butyl OCOOMe 4-pyrimidinyl S n-butyl OCOOMe5-pyrimidinyl S n-butyl OCOOMe 2-indolyl S n-butyl OCOOMe 3-indolyl Sn-butyl OCOOMe 5-indolyl S n-butyl OCOOMe 6-indolyl S n-butyl OCOOMe5-benzimidazolyl S n-butyl OCOOMe 2-benzofuryl S n-butyl OCOOMe3-indazolyl S n-butyl OCOOMe 2-benzoxazolyl S n-butyl OCOOMe4-fluoro-1-naphthyl S n-butyl OCOOMe 5-chloro-2-thienyl S n-butyl OCOOMe4-methyl-1-naphthyl S n-butyl OCOOMe 1-methyl-2-pyrrolyl S n-butylOCOOMe 2-methyl-3-furyl S n-butyl OCOOMe 5-methyl-2-thienyl S n-butylOCOOMe 4-methyl-5-imidazolyl S n-butyl OCOOMe 1-methyl-3-indolyl Sn-butyl OCOOMe 2-methoxy-1-naphthyl S n-butyl OCOOMe3-methoxy-2-naphthyl S n-butyl OCOOMe 6-ethoxy-2-naphthyl S n-butylOCOOMe 5-methoxy-3-indolyl S n-butyl OCOOMe 1,4-dimethoxy-2-naphthyl Sn-butyl OCOOMe 5,6-dimethoxy-2-indolyl S n-butyl OCOOMe5-methoxy-1-methyl-2-indolyl S n-butyl OCOOEt 1-naphthyl S n-butylOCOOEt 2-naphthyl S n-butyl OCOOEt 2-pyrrolyl S n-butyl OCOOEt3-pyrrolyl S n-butyl OCOOEt 2-furyl S n-butyl OCOOEt 3-furyl S n-butylOCOOEt 2-thienyl S n-butyl OCOOEt 3-thienyl S n-butyl OCOOEt 3-pyrazolylS n-butyl OCOOEt 4-pyrazolyl S n-butyl OCOOEt 2-imidazolyl S n-butylOCOOEt 4-imidazolyl S n-butyl OCOOEt 2-oxazolyl S n-butyl OCOOEt4-oxazolyl S n-butyl OCOOEt 5-oxazolyl S n-butyl OCOOEt 2-thiazolyl Sn-butyl OCOOEt 4-thiazolyl S n-butyl OCOOEt 5-thiazolyl S n-butyl OCOOEt2-pyrimidinyl S n-butyl OCOOEt 4-pyrimidinyl S n-butyl OCOOEt5-pyrimidinyl S n-butyl OCOOEt 2-indolyl S n-butyl OCOOEt 3-indolyl Sn-butyl OCOOEt 5-indolyl S n-butyl OCOOEt 6-indolyl S n-butyl OCOOEt5-benzimidazolyl S n-butyl OCOOEt 2-benzofuryl S n-butyl OCOOEt3-indazolyl S n-butyl OCOOEt 2-benzoxazolyl S n-butyl OCOOEt4-fluoro-1-naphthyl S n-butyl OCOOEt 5-chloro-2-thienyl S n-butyl OCOOEt4-methyl-1-naphthyl S n-butyl OCOOEt 1-methyl-2-pyrrolyl S n-butylOCOOEt 2-methyl-3-furyl S n-butyl OCOOEt 5-methyl-2-thienyl S n-butylOCOOEt 4-methyl-5-imidazolyl S n-butyl OCOOEt 1-methyl-3-indolyl Sn-butyl OCOOEt 2-methoxy-2-naphthyl S n-butyl OCOOEt3-methoxy-2-naphthyl S n-butyl OCOOEt 6-ethoxy-2-naphthyl S n-butylOCOOEt 5-methoxy-3-indolyl S n-butyl OCOOEt 1,4-dimethoxy-2-naphthyl Sn-butyl OCOOEt 5,6-dimethoxy-2-indolyl S n-butyl OCOOEt5-methoxy-1-methyl-2-indolyl S n-pentyl OH 1-naphthyl S n-pentyl OH2-naphthyl S n-pentyl OH 2-pyrrolyl S n-pentyl OH 3-pyrrolyl S n-pentylOH 2-furyl S n-pentyl OH 3-furyl S n-pentyl OH 2-thienyl S n-pentyl OH3-thienyl S n-pentyl OH 3-pyrazolyl S n-pentyl OH 4-pyrazolyl S n-pentylOH 2-imidazolyl S n-pentyl OH 4-imidazolyl S n-pentyl OH 2-oxazolyl Sn-pentyl OH 4-oxazolyl S n-pentyl OH 5-oxazolyl S n-pentyl OH2-thiazolyl S n-pentyl OH 4-thiazolyl S n-pentyl OH 5-thiazolyl Sn-pentyl OH 2-pyrimidinyl S n-pentyl OH 4-pyrimidinyl S n-pentyl OH5-pyrimidinyl S n-pentyl OH 2-indolyl S n-pentyl OH 3-indolyl S n-pentylOH 5-indolyl S n-pentyl OH 6-indolyl S n-pentyl OH 5-benzimidazolyl Sn-pentyl OH 2-benzofuryl S n-pentyl OH 3-indazolyl S n-pentyl OH2-benzoxazolyl S n-pentyl OH 4-fluoro-1-naphthyl S n-pentyl OH5-chloro-2-thienyl S n-pentyl OH 4-methyl-1-naphthyl S n-pentyl OH1-methyl-2-pyrrolyl S n-pentyl OH 2-methyl-3-furyl S n-pentyl OH5-methyl-2-thienyl S n-pentyl OH 4-methyl-5-imidazolyl S n-pentyl OH1-methyl-3-indolyl S n-pentyl OH 2-methoxy-1-naphthyl S n-pentyl OH3-methoxy-2-naphthyl S n-pentyl OH 6-ethoxy-2-naphthyl S n-pentyl OH5-methoxy-3-indolyl S n-pentyl OH 1,4-dimethoxy-2-naphthyl S n-pentyl OH5,6-dimethoxy-2-indolyl S n-pentyl OH 5-methoxy-1-methyl-2-indolyl Sn-pentyl OCOOMe 1-naphthyl S n-pentyl OCOOMe 2-naphthyl S n-pentylOCOOMe 2-pyrrolyl S n-pentyl OCOOMe 3-pyrrolyl S n-pentyl OCOOMe 2-furylS n-pentyl OCOOMe 3-furyl S n-pentyl OCOOMe 2-thienyl S n-pentyl OCOOMe3-thienyl S n-pentyl OCOOMe 3-pyrazolyl S n-pentyl OCOOMe 4-pyrazolyl Sn-pentyl OCOOMe 2-imidazolyl S n-pentyl OCOOMe 4-imidazolyl S n-pentylOCOOMe 2-oxazolyl S n-pentyl OCOOMe 4-oxazolyl S n-pentyl OCOOMe5-oxazolyl S n-pentyl OCOOMe 2-thiazolyl S n-pentyl OCOOMe 4-thiazolyl Sn-pentyl OCOOMe 5-thiazolyl S n-pentyl OCOOMe 2-pyrimidinyl S n-pentylOCOOMe 4-pyrimidinyl S n-pentyl OCOOMe 5-pyrimidinyl S n-pentyl OCOOMe2-indolyl S n-pentyl OCOOMe 3-indolyl S n-pentyl OCOOMe 5-indolyl Sn-pentyl OCOOMe 6-indolyl S n-pentyl OCOOMe 5-benzimidazolyl S n-pentylOCOOMe 2-benzofuryl S n-pentyl OCOOMe 3-indazolyl S n-pentyl OCOOMe2-benzoxazolyl S n-pentyl OCOOMe 4-fluoro-1-naphthyl S n-pentyl OCOOMe5-chloro-2-thienyl S n-pentyl OCOOMe 4-methyl-1-naphthyl S n-pentylOCOOMe 1-methyl-2-pyrrolyl S n-pentyl OCOOMe 2-methyl-3-furyl S n-pentylOCOOMe 5-methyl-2-thienyl S n-pentyl OCOOMe 4-methyl-5-imidazolyl Sn-pentyl OCOOMe 1-methyl-3-indolyl S n-pentyl OCOOMe2-methoxy-1-naphthyl S n-pentyl OCOOMe 3-methoxy-2-naphthyl S n-pentylOCOOMe 6-ethoxy-2-naphthyl S n-pentyl OCOOMe 5-methoxy-3-indolyl Sn-pentyl OCOOMe 1,4-dimethoxy-2-naphthyl S n-pentyl OCOOMe5,6-dimethoxy-2-indolyl S n-pentyl OCOOMe 5-methoxy-1-methyl-2-indolyl Sn-pentyl OCOOEt 1-naphthyl S n-pentyl OCOOEt 2-naphthyl S n-pentylOCOOEt 2-pyrrolyl S n-pentyl OCOOEt 3-pyrrolyl S n-pentyl OCOOEt 2-furylS n-pentyl OCOOEt 3-furyl S n-pentyl OCOOEt 2-thienyl S n-pentyl OCOOEt3-thienyl S n-pentyl OCOOEt 3-pyrazolyl S n-pentyl OCOOEt 4-pyrazolyl Sn-pentyl OCOOEt 2-imidazolyl S n-pentyl OCOOEt 4-imidazolyl S n-pentylOCOOEt 2-oxazolyl S n-pentyl OCOOEt 4-oxazolyl S n-pentyl OCOOEt5-oxazolyl S n-pentyl OCOOEt 2-thiazolyl S n-pentyl OCOOEt 4-thiazolyl Sn-pentyl OCOOEt 5-thiazolyl S n-pentyl OCOOEt 2-pyrimidinyl S n-pentylOCOOEt 4-pyrimidinyl S n-pentyl OCOOEt 5-pyrimidinyl S n-pentyl OCOOEt2-indolyl S n-pentyl OCOOEt 3-indolyl S n-pentyl OCOOEt 5-indolyl Sn-pentyl OCOOEt 6-indolyl S n-pentyl OCOOEt 5-benzimidazolyl S n-pentylOCOOEt 2-benzofuryl S n-pentyl OCOOEt 3-indazolyl S n-pentyl OCOOEt2-benzoxazolyl S n-pentyl OCOOEt 4-fluoro-1-naphthyl S n-pentyl OCOOEt5-chloro-2-thienyl S n-pentyl OCOOEt 4-methyl-1-naphthyl S n-pentylOCOOEt 1-methyl-2-pyrrolyl S n-pentyl OCOOEt 2-methyl-3-furyl S n-pentylOCOOEt 5-methyl-2-thienyl S n-pentyl OCOOEt 4-methyl-5-imidazolyl Sn-pentyl OCOOEt 1-methyl-3-indolyl S n-pentyl OCOOEt2-methoxy-1-naphthyl S n-pentyl OCOOEt 3-methoxy-2-naphthyl S n-pentylOCOOEt 6-ethoxy-2-naphthyl S n-pentyl OCOOEt 5-methoxy-3-indolyl Sn-pentyl OCOOEt 1,4-dimethoxy-2-naphthyl S n-pentyl OCOOEt5,6-dimethoxy-2-indolyl S n-pentyl OCOOEt 5-methoxy-1-methyl-2-indolylNH 2-methoxyethyl OH 1-naphthyl NH 2-methoxyethyl OH 2-naphthyl NH2-methoxyethyl OH 2-pyrrolyl NH 2-methoxyethyl OH 3-pyrrolyl NH2-methoxyethyl OH 2-furyl NH 2-methoxyethyl OH 3-furyl NH 2-methoxyethylOH 2-thienyl NH 2-methoxyethyl OH 3-thienyl NH 2-methoxyethyl OH3-pyrazolyl NH 2-methoxyethyl OH 4-pyrazolyl NH 2-methoxyethyl OH2-imidazolyl NH 2-methoxyethyl OH 4-imidazolyl NH 2-methoxyethyl OH2-oxazolyl NH 2-methoxyethyl OH 4-oxazolyl NH 2-methoxyethyl OH5-oxazolyl NH 2-methoxyethyl OH 2-thiazolyl NH 2-methoxyethyl OH4-thiazolyl NH 2-methoxyethyl OH 5-thiazolyl NH 2-methoxyethyl OH2-pyrimidinyl NH 2-methoxyethyl OH 4-pyrimidinyl NH 2-methoxyethyl OH5-pyrimidinyl NH 2-methoxyethyl OH 2-indolyl NH 2-methoxyethyl OH3-indolyl NH 2-methoxyethyl OH 5-indolyl NH 2-methoxyethyl OH 6-indolylNH 2-methoxyethyl OH 5-benzimidazolyl NH 2-methoxyethyl OH 2-benzofurylNH 2-methoxyethyl OH 3-indazolyl NH 2-methoxyethyl OH 2-benzoxazolyl NH2-methoxyethyl OH 4-fluoro-1-naphthyl NH 2-methoxyethyl OH5-chloro-2-thienyl NH 2-methoxyethyl OH 4-methyl-1-naphthyl NH2-methoxyethyl OH 1-methyl-2-pyrrolyl NH 2-methoxyethyl OH2-methyl-3-furyl NH 2-methoxyethyl OH 5-methyl-2-thienyl NH2-methoxyethyl OH 4-methyl-5-imidazolyl NH 2-methoxyethyl OH1-methyl-3-indolyl NH 2-methoxyethyl OH 2-methoxy-1-naphthyl NH2-methoxyethyl OH 3-methoxy-2-naphthyl NH 2-methoxyethyl OH6-ethoxy-2-naphthyl NH 2-methoxyethyl OH 5-methoxy-3-indolyl NH2-methoxyethyl OH 1,4-dimethoxy-2-naphthyl NH 2-methoxyethyl OH5,6-dimethoxy-2-indolyl NH 2-methoxyethyl OH5-methoxy-1-methyl-2-indolyl NH 3-methoxypropyl OH 1-naphthyl NH3-methoxypropyl OH 2-naphthyl NH 3-methoxypropyl OH 2-pyrrolyl NH3-methoxypropyl OH 3-pyrrolyl NH 3-methoxypropyl OH 2-furyl NH3-methoxypropyl OH 3-furyl NH 3-methoxypropyl OH 2-thienyl NH3-methoxypropyl OH 3-thienyl NH 3-methoxypropyl OH 3-pyrazolyl NH3-methoxypropyl OH 4-pyrazolyl NH 3-methoxypropyl OH 2-imidazolyl NH3-methoxypropyl OH 4-imidazolyl NH 3-methoxypropyl OH 2-oxazolyl NH3-methoxypropyl OH 4-oxazolyl NH 3-methoxypropyl OH 5-oxazolyl NH3-methoxypropyl OH 2-thiazolyl NH 3-methoxypropyl OH 4-thiazolyl NH3-methoxypropyl OH 5-thiazolyl NH 3-methoxypropyl OH 2-pyrimidinyl NH3-methoxypropyl OH 4-pyrimidinyl NH 3-methoxypropyl OH 5-pyrimidinyl NH3-methoxypropyl OH 2-indolyl NH 3-methoxypropyl OH 3-indolyl NH3-methoxypropyl OH 5-indolyl NH 3-methoxypropyl OH 6-indolyl NH3-methoxypropyl OH 5-benzimidazolyl NH 3-methoxypropyl OH 2-benzofurylNH 3-methoxypropyl OH 3-indazolyl NH 3-methoxypropyl OH 2-benzoxazolylNH 3-methoxypropyl OH 4-fluoro-1-naphthyl NH 3-methoxypropyl OH5-chloro-2-thienyl NH 3-methoxypropyl OH 4-methyl-1-naphthyl NH3-methoxypropyl OH 1-methyl-2-pyrrolyl NH 3-methoxypropyl OH2-methyl-3-furyl NH 3-methoxypropyl OH 5-methyl-2-thienyl NH3-methoxypropyl OH 4-methyl-5-imidazolyl NH 3-methoxypropyl OH1-methyl-3-indolyl NH 3-methoxypropyl OH 2-methoxy-1-naphthyl NH3-methoxypropyl OH 3-methoxy-2-naphthyl NH 3-methoxypropyl OH6-ethoxy-2-naphthyl NH 3-methoxypropyl OH 5-methoxy-3-indolyl NH3-methoxypropyl OH 1,4-dimethoxy-2-naphthyl NH 3-methoxypropyl OH5,6-dimethoxy-2-indolyl NH 3-methoxypropyl OH5-methoxy-1-methyl-2-indolyl O 2-metboxyethyl OH 1-naphthyl O2-methoxyethyl OH 2-naphthyl O 2-methoxyethyl OH 2-pyrrolyl O2-methoxyethyl OH 3-pyrrolyl O 2-methoxyethyl OH 2-furyl O2-methoxyethyl OH 3-furyl O 2-methoxyethyl OH 2-thienyl O 2-methoxyethylOH 3-thienyl O 2-methoxyethyl OH 3-pyrazolyl O 2-methoxyethyl OH4-pyrazolyl O 2-methoxyethyl OH 2-imidazolyl O 2-methoxyethyl OH4-imidazolyl O 2-methoxyethyl OH 2-oxazolyl O 2-methoxyethyl OH4-oxazolyl O 2-methoxyethyl OH 5-oxazolyl O 2-methoxyethyl OH2-thiazolyl O 2-methoxyethyl OH 4-thiazolyl O 2-methoxyethyl OH5-thiazolyl O 2-methoxyethyl OH 2-pyrimidinyl O 2-methoxyethyl OH4-pyrimidinyl O 2-methoxyethyl OH 5-pyrimidinyl O 2-methoxyethyl OH2-indolyl O 2-methoxyethyl OH 3-indolyl O 2-methoxyethyl OH 5-indolyl O2-methoxyethyl OH 6-indolyl O 2-methoxyethyl OH 5-benzimidazolyl O2-methoxyethyl OH 2-benzofuryl O 2-methoxyethyl OH 3-indazolyl O2-methoxyethyl OH 2-benzoxazolyl O 2-methoxyethyl OH 4-fluoro-1-naphthylO 2-methoxyethyl OH 5-chloro-2-thienyl O 2-methoxyethyl OH4-methyl-1-naphthyl O 2-methoxyethyl OH 1-methyl-2-pyrrolyl O2-methoxyethyl OH 2-methyl-3-furyl O 2-methoxyethyl OH5-methyl-2-thienyl O 2-methoxyethyl OH 4-methyl-5-imidazolyl O2-methoxyethyl OH 1-methyl-3-indolyl O 2-methoxyethyl OH2-methoxy-1-naphthyl O 2-methoxyethyl OH 3-methoxy-2-naphthyl O2-methoxyethyl OH 6-ethoxy-2-naphthyl O 2-methoxyethyl OH5-methoxy-3-indolyl O 2-methoxyethyl OH 1,4-dimethoxy-2-naphthyl O2-methoxyethyl OH 5,6-dimethoxy-2-indolyl O 2-methoxyethyl OH5-methoxy-1-methyl-2-indolyl O 3-methoxypropyl OH 1-naphthyl O3-methoxypropyl OH 2-naphthyl O 3-methoxypropyl OH 2-pyrrolyl O3-methoxypropyl OH 3-pyrrolyl O 3-methoxypropyl OH 2-furyl O3-methoxypropyl OH 3-furyl O 3-methoxypropyl OH 2-thienyl O3-methoxypropyl OH 3-thienyl O 3-methoxypropyl OH 3-pyrazolyl O3-methoxypropyl OH 4-pyrazolyl O 3-methoxypropyl OH 2-imidazolyl O3-methoxypropyl OH 4-imidazolyl O 3-methoxypropyl OH 2-oxazolyl O3-methoxypropyl OH 4-oxazolyl O 3-methoxypropyl OH 5-oxazolyl O3-methoxypropyl OH 2-thiazolyl O 3-methoxypropyl OH 4-thiazolyl O3-methoxypropyl OH 5-thiazolyl O 3-methoxypropyl OH 2-pyrimidinyl O3-methoxypropyl OH 4-pyrimidinyl O 3-methoxypropyl OH 5-pyrimidinyl O3-methoxypropyl OH 2-indolyl O 3-methoxypropyl OH 3-indolyl O3-methoxypropyl OH 5-indolyl O 3-methoxypropyl OH 6-indolyl O3-methoxypropyl OH 5-benzimidazolyl O 3-methoxypropyl OH 2-benzofuryl O3-methoxypropyl OH 3-indazolyl O 3-methoxypropyl OH 2-benzoxazolyl O3-methoxypropyl OH 4-fluoro-1-naphthyl O 3-methoxypropyl OH5-chloro-2-thienyl O 3-methoxypropyl OH 4-methyl-1-naphthyl O3-methoxypropyl OH 1-methyl-2-pyrrolyl O 3-methoxypropyl OH2-methyl-3-furyl O 3-methoxypropyl OH 5-methyl-2-thienyl O3-methoxypropyl OH 4-methyl-5-imidazolyl O 3-methoxypropyl OH1-methyl-3-indolyl O 3-methoxypropyl OH 2-methoxy-1-naphthyl O3-methoxypropyl OH 3-methoxy-2-naphthyl O 3-methoxypropyl OH6-ethoxy-2-naphthyl O 3-methoxypropyl OH 5-methoxy-3-indolyl O3-methoxypropyl OH 1,4-dimethoxy-2-naphthyl O 3-methoxypropyl OH5,6-dimethoxy-2-indolyl O 3-methoxypropyl OH5-methoxy-1-methyl-2-indolyl S 2-methoxyethyl OH 1-naphthyl S2-methoxyethyl OH 2-naphthyl S 2-methoxyethyl OH 2-pyrrolyl S2-methoxyethyl OH 3-pyrrolyl S 2-methoxyethyl OH 2-furyl S2-methoxyethyl OH 3-furyl S 2-methoxyethyl OH 2-thienyl S 2-methoxyethylOH 3-thienyl S 2-methoxyethyl OH 3-pyrazolyl S 2-methoxyethyl OH4-pyrazolyl S 2-methoxyethyl OH 2-imidazolyl S 2-methoxyethyl OH4-imidazolyl S 2-methoxyethyl OH 2-oxazolyl S 2-methoxyethyl OH4-oxazolyl S 2-methoxyethyl OH 5-oxazolyl S 2-methoxyethyl OH2-thiazolyl S 2-methoxyethyl OH 4-thiazolyl S 2-methoxyethyl OH5-thiazolyl S 2-methoxyethyl OH 2-pyrimidinyl S 2-methoxyethyl OH4-pyrimidinyl S 2-methoxyethyl OH 5-pyrimidinyl S 2-methoxyethyl OH2-indolyl S 2-methoxyethyl OH 3-indolyl S 2-methoxyethyl OH 5-indolyl S2-methoxyethyl OH 6-indolyl S 2-methoxyethyl OH 5-benzimidazolyl S2-methoxyethyl OH 2-benzofuryl S 2-methoxyethyl OH 3-indazolyl S2-methoxyethyl OH 2-benzoxazolyl S 2-methoxyethyl OH 4-fluoro-1-naphthylS 2-methoxyethyl OH 5-chloro-2-thienyl S 2-methoxyethyl OH4-methyl-1-naphthyl S 2-methoxyethyl OH 1-methyl-2-pyrrolyl S2-methoxyethyl OH 2-methyl-3-furyl S 2-methoxyethyl OH5-methyl-2-thienyl S 2-methoxyethyl OH 4-methyl-5-imidazolyl S2-methoxyethyl OH 1-methyl-3-indolyl S 2-methoxyethyl OH2-methoxy-1-naphthyl S 2-methoxyethyl OH 3-methoxy-2-naphthyl S2-methoxyethyl OH 6-ethoxy-2-naphthyl S 2-methoxyethyl OH5-methoxy-3-indolyl S 2-methoxyethyl OH 1,4-dimethoxy-2-naphthyl S2-methoxyethyl OH 5,6-dimethoxy-2-indolyl S 2-methoxyethyl OH5-methoxy-1-methyl-2-indolyl S 2-hydroxyethyl OH 1-naphthyl S2-hydroxyethyl OH 2-naphthyl S 2-hydroxyethyl OH 2-pyrrolyl S2-hydroxyethyl OH 3-pyrrolyl S 2-hydroxyethyl OH 2-furyl S2-hydroxyethyl OH 3-furyl S 2-hydroxyethyl OH 2-thienyl S 2-hydroxyethylOH 3-thienyl S 2-hydroxyethyl OH 3-pyrazolyl S 2-hydroxyethyl OH4-pyrazolyl S 2-hydroxyethyl OH 2-imidazolyl S 2-hydroxyethyl OH4-imidazolyl S 2-hydroxyethyl OH 2-oxazolyl S 2-hydroxyethyl OH4-oxazolyl S 2-hydroxyethyl OH 5-oxazolyl S 2-hydroxyethyl OH2-thiazolyl S 2-hydroxyethyl OH 4-thiazolyl S 2-hydroxyethyl OH5-thiazolyl S 2-hydroxyethyl OH 2-pyrimidinyl S 2-hydroxyethyl OH4-pyrimidinyl S 2-hydroxyethyl OH 5-pyrimidinyl S 2-hydroxyethyl OH2-indolyl S 2-hydroxyethyl OH 3-indolyl S 2-hydroxyethyl OH 5-indolyl S2-hydroxyethyl OH 6-indolyl S 2-hydroxyethyl OH 5-benzimidazolyl S2-hydroxyethyl OH 2-benzofuryl S 2-hydroxyethyl OH 3-indazolyl S2-hydroxyethyl OH 2-benzoxazolyl S 2-hydroxyethyl OH 4-fluoro-1-naphthylS 2-hydroxyethyl OH 5-chloro-2-thienyl S 2-hydroxyethyl OH4-methyl-1-naphthyl S 2-hydroxyethyl OH 1-methyl-2-pyrrolyl S2-hydroxyethyl OH 2-methyl-3-furyl S 2-hydroxyethyl OH5-methyl-2-thienyl S 2-hydroxyethyl OH 4-methyl-5-imidazolyl S2-hydroxyethyl OH 1-methyl-3-indolyl S 2-hydroxyethyl OH2-methoxy-1-naphthyl S 2-hydroxyethyl OH 3-methoxy-2-naphthyl S2-hydroxyethyl OH 6-ethoxy-2-naphthyl S 2-hydroxyethyl OH5-methoxy-3-indolyl S 2-hydroxyethyl OH 1,4-dimethoxy-2-naphthyl S2-hydroxyethyl OH 5,6-dimethoxy-2-indolyl S 2-hydroxyethyl OH5-methoxy-1-methyl-2-indolyl

A compound in which R² represents acyloxy or alkoxycarbonyloxy accordingto the present invention is equivalent to ester of a compound in whichR² represents hydroxyl. The compound is a prodrug that is aimed atimproving solubility, absorbency, and biostability of a compound inwhich R² represents hydroxyl. That is, the above ester is metabolized ina living organism to an active form compound in which R² is hydroxyl. Acompound represented by general formula (I) and a tautomer thereof arechemically equivalent. The adenine derivative according to the presentinvention includes the tautomer. For example, when R² representhydroxyl, a compound represented by general formula (I) is a hydroxyderivative represented by general formula (II):

wherein R¹, X, and Y are as defined in general formula (I). An exampleof a tautomer of this derivative is an oxo derivative represented bygeneral formula (III):

wherein R¹, X, and Y are as defined in general formula (I).

An embodiment of a process for producing these adenine derivatives ishereafter described in detail.

(1) When R² is OH

A compound (IV) is allowed to react with Y—CH₂-Hal (wherein Y is asdefined in general formula (II) and Hal represents a halogen atom) inthe presence of a base, thereby synthesizing a 9-substitution product(V). Examples of the aforementioned bases that can be used includealkali metal salt or alkaline earth metal salt of carbonic acid such aspotassium carbonate, metal hydroxides such as sodium hydroxide andpotassium hydroxide, metal hydrides such as sodium hydride, andalkoxides such as potassum t-butoxide. Examples of the aforementionedsolvents that can be used include aprotic solvents such asdimethylformamide, dimethyl sulfoxide, tetrahydrofuran, and 1,4-dioxane.Reaction temperature can be between room temperature and refluxtemperature of the solvent.

Subsequently, when X represents NH, a compound (V) is allowed to reactwith a corresponding R¹—NH₂ (wherein R¹ is as defined above) in thepresence or absence of a base, thereby synthesizing a 2-substitutionproduct (VI). Examples of bases that can be used include tertiary aminessuch as triethylamine, diisopropylethylamine, and4-dimethylaminopyridine. Examples of solvents that can be used includeaprotic solvents, such as tetrahydrofuran, 1,4-dioxane, and diglyme, andalcoholic solvents such as propanol or butanol. Alternatively, reactionmay be carried out in the absence of a solvent. Reaction temperature canbe between 50° C. and reflux temperature of the solvent.

When X represents an oxygen atom or sulfur atom, a compound (V) isallowed to react with a corresponding R¹—OH or R¹—SH in the presence ofa base, thereby synthesizing a 2-substitution product (VI). Examples ofbases that can be used include alkali metals such as sodium or potassiumand alkali metal hydrides such as sodium hydride. Examples of solventsthat can be used include aprotic solvents such as dimethylformamide,dimethyl sulfoxide, tetrahydrofuran, 1,4-dioxane, and diglyme.Alternatively, reaction may be carried out in the absence of a solvent.Reaction temperature can be between 50° C. and reflux temperature of thesolvent.

In a process for producing a compound (VI) from a compound (IV), acompound (VI) can be obtained by first synthesizing a 2-substitutionproduct (V′), followed by the reaction between the 2-substitutionproduct (V′) and Y—CH₂-Hal (wherein Y is as defined in general formula(II) and Hal represents a halogen atom).

A compound (VII) can be synthesized by reacting a compound (VI) withbromine. Examples of solvents that can be used include, halogenatedsolvents such as carbon tetrachloride, dichloromethane or chloroform,and acetic acid. Reaction temperature can be between 0° C. and refluxtemperature of the solvent. Alternatively, a reaction assistant such assodium acetate may be additionally used in the reaction.

A compound (IX) can be synthesized through hydrolysis of a compound(VII) under acidic conditions. Examples of acids that can be usedinclude hydrochloric acid and hydrobromic acid. Reaction temperature canbe between 50° C. and reflux temperature of the solvent. Alternatively,a compound (VII) is allowed to react with sodium methoxide to prepare acompound (VIII), and the resultant is treated with acid fordemethylation. Thus, a compound (IX) can be obtained.

A compound (X) can be synthesized by reacting a compound (VII) withsodium hydrosulfide (sodium hydrogensulfide). Examples of solvents thatcan be used include alcoholic solvents such as ethanol, propanol, andbutanol. Reaction temperature can be between 50° C. and refluxtemperature of the solvent.

A compound (XI) can be obtained by allowing the compound (IX) to reactwith acyl chloride or chloroformate ester corresponding to R² in thepresence of a base. Examples of bases that can be used include tertiaryamines such as triethylamine, diisopropylethylamine, or4-dimethylaminopyridine. Examples of solvents that can be used includeaprotic solvents such as tetrahydrofuran, 1,4-dioxane, anddichloromethane. Reaction temperature can be between 0° C. and refluxtemperature of the solvent (In the formula, R⁴ represents C₁₋₇ alkyl orC₁₋₇ alkoxy).

The thus obtained adenine derivative according to the present inventioncan be used as a pharmaceutically acceptable salt such as sodium salt,potassium salt, calcium salt, hydrochloride, hydrobromate, sulfate,nitrate, acetate, methanesulfonate, toluenesulfonate, citrate, fumarate,or maleate.

The adenine derivative according to the present invention is useful as atherapeutic agent for viral diseases such as hepatitis B, hepatitis C,and AIDS, cancerous diseases, and diseases resulting from type 2 helperT cells. It can be used in various dosage forms, for example, oralpreparations such as a tablet, capsule, or powder. In addition, it canbe parenteral injection or external preparation. The pharmaceuticalpreparation according to the present invention can be any substanceselected from the group consisting of a compound represented by generalformula (I), a tautomer thereof, and a pharmaceutically acceptable saltthereof. A hydrate or solvate thereof may also be used. Alternatively,two or more of these substances may be used in combinations. A substanceitself that is selected from the aforementioned group may beadministered as a pharmaceutical preparation according to the presentinvention. In general, however, it is preferably administered in a formof a pharmaceutical composition comprising, as an active ingredient, theaforementioned substance and a pharmaceutically acceptable additive forpharmaceutical preparations.

A pharmaceutical composition for organisms can be easily produced inaccordance with a process that is common in the field of pharmaceuticalpreparations, wherein the aforementioned substance as an activeingredient is mixed with at least one pharmaceutically acceptableadditive for pharmaceutical preparations. A route for administering thepharmaceutical preparation according to the present invention is notparticularly limited. Preferably, the most effective route is suitablyselected for therapy and/or prevention. Examples of pharmaceuticalcompositions that are suitable for oral administration include capsules,powders, tablets, granules, fine grains, syrups, liquids, andsuspensions. Examples of pharmaceutical compositions that are suitablefor parenteral administration include inhalants, sprays, intrarectalpreparations, parenteral injections, drops, pastes, creams, percutaneousabsorbents, transmucosal absorbents, eye drops, nasal drops, ear drops,tapes, and medical applications. It should be noted that the forms ofthe pharmaceutical preparation according to the present invention arenot limited thereto.

Among the pharmaceutical compositions suitable for oral administration,for example, liquid preparations such as emulsions and syrups can beproduced using additives for pharmaceutical preparations. Examplesthereof include: water; saccharine such as sucrose, sorbit, andfructose; glycols such as polyethylene glycol and propylene glycol; oilssuch as sesame oil, olive oil, and soybean oil; antiseptics such asp-hydroxybenzoate; and flavors such as strawberry flavor and peppermint.Solid preparations such as capsules, tablets, powders, and granules canbe produced using: for example, excipients such as lactose, glucose,sucrose, and mannite; disintegrators such as starch and sodium alginate;lubricants such as magnesium stearate and talc; binders such aspolyvinyl alcohol, hydroxypropylcellulose, and gelatin; surfactants suchas fatty acid ester; and plasticizers such as glycerin.

Among pharmaceutical compositions suitable for parenteraladministration, liquid preparations such as parenteral injections,drops, and eye drops can be preferably produced as sterilized isotonicliquid preparations. For example, parenteral injections can be producedusing an aqueous medium comprising a mixture of a salt solution, aglucose solution, or salt water and a glucose solution. Intrarectalpreparations can be generally produced in a form of suppository using,for example, a carrier such as cacao butter, hydrogenated fat, orhydrogenated carboxylic acid. Sprays can be prepared using nonirritatingcarriers that allow the aforementioned substances as active ingredientsto be dispersed as fine particles to facilitate absorption. Examples ofsuch carriers include lactose and glycerin. A form of aerosol or drypowder preparation can be selected. Also, at least one additive forpharmaceutical preparations selected from diluent, flavor, antiseptics,excipient, disintegrator, lubricant, binder, surfactant, plasticizer,and the like as exemplified in the production of oral preparation can besuitably used to produce a pharmaceutical composition for parenteraladministration. It should be noted that additives for pharmaceuticalpreparations that are used to produce the pharmaceutical preparationaccording to the present invention are not limited to the aforementionedsubstances. Any substance can be used as long as it is available topersons skilled in the art.

The dose of the adenine derivative according to the present invention issuitably determined depending on, for example, sex, age, body weight,type of disease, or symptom of a patient. The dose is generally in therange of 0.001 to 100 mg/kg per day, and preferably in the range of 0.01to 10 mg/kg. Administration can be made in single or several separatedoses.

This description includes part or all of the content as disclosed in thedescription of Japanese Patent Application No. 2001-118232, which is apriority document of the present application.

BRIEF DESCRIPTION OF DRAWINGS

FIG. 1 is a diagram showing the result of evaluation for the medicinaleffect of the compound according to the present invention in a rat modelof eosinophil leukocytic infiltration.

FIG. 2 is a diagram showing the result of evaluation for the medicinaleffect of the compound according to the present invention in a mousemodel of active cutaneous anaphylaxis.

FIG. 3 is a diagram showing the result of evaluation for the antitumoreffect described in Example 65, wherein the tumor volume of the compoundof Example 27 and that of mouse interferon α were compared with that ofthe vehicle (a control group).

FIG. 4 is a diagram showing the result of evaluation for the antitumoreffect described in Example 66 (the effect of inhibiting metastasis),wherein the wet weight of each lymph node was compared among the groupto which the vehicle was administered (the control group), the group towhich mouse interferon α was administered, and the group to which thecompound of Example 27 was administered.

BEST MODES FOR CARRYING OUT THE INVENTION

The present invention is hereafter described in detail with reference tothe examples, although the technical scope of the present invention isnot limited thereto.

Reference Example 1 2-Butoxyadenine

Sodium (13.6 g, 0.59 mol) was added to butanol (480 ml), the temperatureof the mixture was raised to 90° C. to completely dissolve sodiumtherein. Subsequently, 2-chloroadenine (4.0 g, 23.6 mmol) was added, andthe resultant was heated under reflux for 9 hours. After the reactionsolution was cooled to 4° C., water (400 ml) was added thereto, and theresultant was vigorously stirred for 30 minutes. The separated layer ofbutanol was concentrated under reduced pressure, water (400 ml) wasadded to the residue, and concentrated hydrochloric acid was addeddropwide under ice cooling to neutralize the product. The precipitatedsolid was collected by filtration, the resulting solid was added toethanol (70 ml), and the resultant was heated under reflux for 30minutes. The product was cooled to room temperature, and theprecipitated solid was then collected by filtration. Thus, 3.72 g of thetitle compound was obtained (yield: 76%).

Reference Example 2 8-Bromo-2-butoxy-9-(6-chloro-3-pyridylmethyl)adenine

Potassium carbonate (2.85 g, 20.6 mmol) and2-chloro-5-chloromethylpyridine (3.33 g, 20.6 mmol) were added to theDMF solution (125 ml) of 2-butoxyadenine (2.60 g, 12.5 mmol) obtained inReference Example 1. The resultant was stirred while heating at 80° C.for 2.5 hours. The reaction solution was concentrated under reducedpressure, water (100 ml) was added thereto, and the resultant wasneutralized with 1N hydrochloric acid. The precipitated solid wascollected by filtration. The resulting solid was dissolved in methylenechloride (100 ml), hexane (150 ml) was added under ice cooling, and theprecipitated crystal was collected by filtration. Thus,2-butoxy-9-(6-chloro-3-pyridylmethyl)adenine was obtained (yield: 3.12g). Bromine (1.92 ml, 37.5 mmol) was added to an acetic acid suspension(186 ml) comprising sodium acetate (3.05 g, 37.2 mmol) and2-butoxy-9-(6-chloro-3-pyridylmethyl)adenine (3.1 g, 9.31 mmol) at roomtemperature, and the resultant was allowed to react for 4 hours. Thereaction solution was removed by distillation under reduced pressure,water (200 ml) was added to the residue, and the resultant wasneutralized with 5N sodium hydroxide under ice cooling. The precipitatedcrystal was collected by filtration, and crude crystal was recrystalizedwith the aid of methanol. The resultant was dried under reduced pressureat 40° C. for 15 hours. Thus, 2.38 g of the title compound was obtainedas a white powdery crystal (yield: 62%).

Reference Example 32-Butoxy-9-(6-chloro-3-pyridylmethyl)-8-methoxyadenine

Sodium (614 mg, 26.7 mmol) was added and completely dissolved inmethanol (110 ml). 8-Bromo-2-butoxy-9-(6-chloro-3-pyridylmethyl)adenine(2.2 g, 5.34 mmol) obtained in Reference Example 2 was added to theresulting solution, and the mixture was heated under reflux for 3.5hours. The reaction solution was concentrated under reduced pressure,water (100 ml) was added to the residue, and the resultant wasneutralized with concentrated hydrochloric acid under ice cooling. Theprecipitated solid was collected by filtration and washed with water (20ml). This solid was recrystalized with the aid of ethyl acetate (30 ml)to obtain 1.26 g of the title compound as a white powdery crystal(yield: 65.0%).

Reference Example 4 2-Butoxy-9-(6-methoxy-3-pyridylmethyl)adenine

Sodium (415 mg, 18.0 mmol) was added and completely dissolved inmethanol (18 ml). Thereafter,2-butoxy-9-(6-chloro-3-pyridylmethyl)adenine (300 mg, 0.90 mmol) wasadded thereto, and the resultant was heated under reflux for 24 hours.The reaction solution was concentrated under reduced pressure, water (30ml) was added to the residue, and the resultant was neutralized withconcentrated hydrochloric acid under ice cooling. The precipitated solidwas collected by filtration, and crude crystal was purified by silicagel column chromatography (methylene chloride:methanol=50:1) to obtain148 mg of the title compound (yield: 50%).

Reference Example 5 2-Butylaminoadenine

2-Chloroadenine (6.0 g, 35.4 mmol) and butylamine (30 ml) were placed inan autoclave (200 ml), and the content of the autoclave was allowed toreact at 130° C. for 150 hours. The reaction solution was concentratedunder reduced pressure, and water was poured into the residue toprecipitate a solid. The precipitated solid was sequentially washed withmethylene chloride and methanol. Thus, 2.08 g of the title compound wasobtained as a yellowish orange powdery solid (yield: 30%).

EXAMPLE 1 2-Butoxy-9-(6-chloro-3-pyridylmethyl)-8-hydroxyadenine

The compound (1.26 g, 3.47 mmol) obtained in Reference Example 3 wasadded to concentrated hydrochloric acid (70 ml), and the mixture wasallowed to react at room temperature for 2 hours. The reaction solutionwas concentrated under reduced pressure, water (130 ml) was added to theresidue, and the resultant was neutralized with an aqueous solution of5N sodium hydroxide under ice cooling. The precipitated crystal wascollected by filtration and then dried. Thus, 1.20 g of the titlecompound was obtained as a white powdery crystal (yield: 99%).

¹H NMR (DMSO-d₆) δ 10.14 (1H, brs), 8.40 (1H, d, J=2.4 Hz), 7.76 (1H,dd, J=2.4, 8.4 Hz), 7.49 (1H, d, J=8.4 Hz), 6.55 (2H, brs), 4.91 (2H,s), 4.14 (2H, t, J=6.5 Hz), 1.67–1.57 (2H, m), 1.44–1.30 (2H, m), 0.90(3H, t, J=7.3 Hz).

EXAMPLE 2 2-Butoxy-8-hydroxy-9-(6-methoxy-3-pyridylmethyl)adenine

The title compound was obtained in the same manner as in Example 1 usinga corresponding starting material.

¹H NMR (DMSO-d₆) δ 10.09 (1H, brs), 8.16 (1H, d, J=2.4 Hz), 7.65 (1H,dd, J=2.4, 8.4 Hz), 6.78 (1H, d, J=8.4 Hz), 6.49 (2H, brs), 4.80 (2H,s), 4.15 (2H, t, J=6.6 Hz), 3.81 (3H, s), 1.66–1.58 (2H, m), 1.42–1.34(2H, m), 0.91 (3H, t, J=7.3 Hz).

EXAMPLE 3 2-Butoxy-9-(6-ethoxy-3-pyridylmethyl)-8-hydroxyadenine

The title compound was obtained in the same manner as in Example 1 usinga corresponding starting material.

¹H NMR (DMSO-d₆) δ 10.06 (1H, brs), 8.14 (1H, d, J=2.4 Hz), 7.64 (1H,dd, J=2.4, 8.6 Hz), 6.75 (1H, d, J=8.6 Hz), 6.48 (2H, brs), 4.80 (2H,s), 4.26 (2H, q, J=7.2 Hz), 4.15 (2H, t, J=6.6 Hz), 1.68–1.58 (2H, m),1.42–1.34 (2H, m), 1.28 (3H, t, J=7.2 Hz), 0.91 (3H, t, J=7.3 Hz).

EXAMPLE 4 2-Butoxy-9-(6-n-butoxy-3-pyridylmethyl)-8-hydroxyadenine

The title compound was obtained in the same manner as in Example 1 usinga corresponding starting material.

¹H NMR (DMSO-d₆) δ 10.25 (1H, brs), 8.13 (1H, d, J=1.9 Hz), 7.63 (1H,dd, J=1.9, 8.4 Hz), 6.75 (1H, d, J=8.4 Hz), 6.53 (2H, brs), 4.79 (2H,s), 4.23–4.12 (4H, m), 1.68–1.60 (4H, m), 1.42–1.34 (4H, m), 0.94–0.88(6H, m).

EXAMPLE 5 2-Butoxy-9-(2-chloro-3-pyridylmethyl)-8-hydroxyadenine

The title compound was obtained in the same manner as in Example 1 usinga corresponding starting material.

¹H NMR (DMSO-d₆) δ 10.15 (1H, brs), 8.36–8.33 (1H, m), 7.52–7.50 (1H,m), 7.41–7.36 (1H, m), 6.53 (2H, brs), 4.94 (2H, s), 4.07 (2H, t, J=6.6Hz), 1.62–1.52 (2H,m), 1.37–1.23 (2H, m), 0.87 (3H, t, J=7.3 Hz).

EXAMPLE 6 2-Butoxy-8-hydroxy-9-(2-methoxy-3-pyridylmethyl)adenine

The title compound was obtained in the same manner as in Example 1 usinga corresponding starting material.

¹H NMR (DMSO-d₆) δ 10.06 (1H, brs), 8.08–8.06 (1H, m), 7.21–7.19 (1H,m), 6.93–6.88 (1H, m), 6.47 (2H, brs), 4.80 (2H, s), 4.08 (2H, t, J=6.5Hz), 3.92 (3H, s), 1.60–1.52 (2H, m), 1.38–1.29 (2H, m), 0.87 (3H, t,J=7.3 Hz).

EXAMPLE 72-Butoxy-9-(6-chloro-5-methoxy-3-pyridylmethyl)-8-hydroxyadenine

The title compound was obtained in the same manner as in Example 1 usinga corresponding starting material.

¹H NMR (DMSO-d₆) δ 10.06 (1H, brs), 8.12 (1H, d, J=1.9 Hz), 7.85 (1H, d,J=1.9 Hz), 6.49 (2H, brs), 4.83 (2H, s), 4.16 (2H, t, J=6.6 Hz), 3.91(3H, s), 1.66–1.61 (2H, m), 1.42–1.34 (2H, m), 0.91 (3H, t, J=7.3 Hz).

EXAMPLE 8 2-Butoxy-8-hydroxy-9-(3-pyridylmethyl)adenine

Potassium carbonate (1.1 g, 8 mmol) and 3-chloromethylpyridinehydrochloride (660 mg, 5 mmol) were added to a DMF solution (30 ml)comprising 2-chloroadenine (520 mg, 3 mmol), and the resultant wasstirred while heating at 80° C. for 3 hours. The reaction solution wasconcentrated under reduced pressure, water was added thereto, and theprecipitated solid was collected by filtration. Thus,2-chloro-9-(3-pyridylmethyl)adenine was obtained (yield: 759 mg). Sodium(750 mg, 30 mmol) was added to butanol (50 ml), and the temperature ofthe mixture was raised to 90° C. to completely dissolve sodium therein.Subsequently, 2-chloro-9-(3-pyridylmethyl)adenine (430 mg, 1.5 mmol) wasadded thereto, and the resultant was heated under reflux for 2 hours.The solvent was concentrated under reduced pressure, water was added tothe residue, and concentrated hydrochloric acid was added dropwise underice cooling to neutralize the solution. Liquid separation was carriedout with the addition of methylene chloride, and the organic layer wasconcentrated under reduced pressure. Acetic acid (30 ml) was added tothe residue to dissolve it, bromine (660 mg, 5.5 mmol) was addedthereto, and the resultant was allowed to react at room temperature allday and night. The reaction solution was removed by distillation underreduced pressure, and the residue was purified by silica gel columnchromatography (methylene chloride:methanol=10:1). Thus, 310 mg of8-bromo-2-butoxy-9-(3-pyridylmethyl)adenine was obtained. Subsequently,the title compound was obtained in the same manner as in ReferenceExample 3 and Example 1.

¹H NMR (DMSO-d₆) δ 10.22 (1H, brs), 8.56 (1H, d, J=1.9 Hz), 8.49–8.47(1H, m), 7.71–7.67 (1H, m), 7.38–7.33 (1H, m), 6.54 (2H, brs), 4.90 (2H,s), 4.14 (2H, t, J=6.6 Hz), 1.65–1.57 (2H, m), 1.41–1.33 (2H, m), 0.90(3H, t, J=7.3 Hz).

EXAMPLE 9 2-Butoxy-8-hydroxy-9-(4-pyridylmethyl)adenine

The title compound was obtained in the same manner as in Example 1 usinga corresponding starting material.

¹H NMR (DMSO-d₆) δ 10.20 (1H, brs), 8.70–8.68 (2H, m), 7.29–7.27 (2H,m), 6.48 (2H, brs), 4.92 (2H, s), 4.16 (2H, t, J=6.6 Hz), 1.63–1.55 (2H,m), 1.40–1.32 (2H, m), 0.89 (3H, t, J=7.3 Hz).

EXAMPLE 10 2-Butoxy-9-(pyrazin-2-ylmethyl)-8-methoxyadenine

The title compound was obtained in the same manner as in Example 1 usinga corresponding starting material.

¹H NMR (DMSO-d₆) δ 10.02 (1H, brs), 8.66 (1H, s), 8.56–8.53 (2H, m),6.48 (2H, brs), 5.05 (2H, s), 4.06 (2H, t, J=6.6 Hz), 1.59–1.51 (2H, m),1.37–1.29 (2H, m), 0.87 (3H, t, J=7.3 Hz).

EXAMPLE 11 2-Butoxy-9-(5,6-dichloro-3-pyridylmethyl)-8-hydroxyadenine

Concentrated hydrochloric acid (4 ml) was added to a butanol suspension(4 ml) comprising2-n-butoxy-8-bromo-9-(5,6-dichloro-3-pyridylmethyl)-8-hydroxyadenine(150 mg, 0.34 mmol) obtained in the same manner as in Reference Example2, and the resultant was allowed to react at 70° C. for 9 hours. Thereaction solution was concentrated under reduced pressure, water (30 ml)was added to the residue under ice cooling, and the solution wasneutralized with an aqueous solution of 1N sodium hydroxide. Theprecipitated solid was collected by filtration, crude crystal waspurified by silica gel column chromatography (methylenechloride:methanol=25:1), and 45 mg of the title compound was obtained asa white powdery crystal (yield: 35%).

¹H NMR (DMSO-d₆) δ 10.16 (1H, brs), 8.36 (1H, d, J=1.9 Hz), 8.06 (1H, d,J=1.9 Hz), 6.52 (2H, brs), 4.93 (2H, s), 4.13 (2H, t, J=6.6 Hz),1.64–1.58 (2H, m), 1.40–1.32 (2H, m), 0.90 (3H, t, J=7.3 Hz).

EXAMPLE 12 2-Butoxy-9-(2,6-dichloro-3-pyridylmethyl)-8-hydroxyadenine

The title compound was obtained in the same manner as in Example 11using a corresponding starting material.

¹H NMR (DMSO-d₆) δ 10.12 (1H, brs), 7.66 (1H, d, J=8.4 Hz), 7.52 (1H, d,J=8.4 Hz), 6.52 (2H, brs), 4.92 (2H, s), 4.08 (2H, t, J=6.6 Hz),1.60–1.52 (2H, m), 1.37–1.29 (2H, m), 0.88 (3H, t, J=7.4 Hz).

EXAMPLE 13 2-Butoxy-9-(6-piperidino-3-pyridylmethyl)-8-hydroxyadenine

The compound (100 mg, 0.29 mmol) obtained in Example 1 was added topiperidine (3 ml), and the resultant was allowed to react at 90° C. for30 hours. The reaction solution was concentrated under reduced pressure,and methylene chloride (50 ml) was added to the residue to precipitate asolid. The precipitated solid was collected by filtration and washedwith water. Thus, 56 mg of the title compound was obtained as a whitepowdery solid (yield: 49%).

¹H NMR (DMSO-d₆) δ 9.79 (1H, brs), 8.09 (1H, d, J=2.4 Hz), 7.47 (1H, dd,J=2.4, 8.6 Hz), 6.75 (1H, d, J=8.6 Hz), 6.44 (2H, brs), 4.70 (2H, s),4.17 (2H, t, J=6.5 Hz), 3.48–3.44 (4H, m), 1.67–1.35 (10H, m), 0.92 (3H,t, J=7.3 Hz).

EXAMPLE 142-Butoxy-9-(6-(1-pyrrolidinyl)-3-pyridylmethyl)-8-hydroxyadenine

The title compound was obtained in the same manner as in Example 13using the compound obtained in Example 1 and pyrrolidine.

¹H NMR (DMSO-d₆) δ 10.03 (1H, brs), 8.07 (1H, d, J=2.4 Hz), 7.46 (1H,dd, J=2.4, 8.6 Hz), 6.45 (2H, brs), 6.37 (1H, d, J=8.6 Hz), 4.69 (2H,s), 4.16 (2H, t, J=6.6 Hz), 3.33–3.29 (4H, m), 1.93–1.88 (4H, m),1.67–1.59 (2H, m), 1.43–1.35 (2H, m), 0.92 (3H, t, J=7.3 Hz).

EXAMPLE 15 2-Butoxy-9-(6-morpholino-3-pyridylmethyl)-8-hydroxyadenine

The title compound was obtained in the same manner as in Example 13using the compound obtained in Example 1 and morpholine.

¹H NMR (DMSO-d₆) δ 10.01 (1H, brs), 8.14 (1H, d, J=2.4 Hz), 7.53 (1H,dd, J=2.4, 8.6 Hz), 6.78 (1H, d, J=8.6 Hz), 6.45 (2H, brs), 4.73 (2H,s), 4.16 (2H, t, J=6.6 Hz), 3.66 (4H, t, J=4.9 Hz), 3.38 (4H, t, J=4.9Hz), 1.67–1.61 (2H, m), 1.43–1.35 (2H, m), 0.92 (3H, t, J=7.3 Hz).

EXAMPLE 16 2-Butoxy-9-(6-dimethylamino-3-pyridylmethyl)-8-hydroxyadenine

The title compound was obtained in the same manner as in Example 13using the compound obtained in Example 1 and an aqueous solution of 40%dimethylamine.

¹H NMR (DMSO-d₆) δ 10.12 (1H, brs), 8.09 (1H, d, J=2.4 Hz), 7.48 (1H,dd, J=2.4, 8.9 Hz), 6.57 (1H, d, J=8.9 Hz), 6.49 (2H, brs), 4.70 (2H,s), 4.16 (2H, t, J=6.6 Hz), 2.97 (6H, s), 1.70–1.46 (2H, m), 1.43–1.33(2H, m), 0.92 (3H, t, J=7.3 Hz).

EXAMPLE 17 2-Butylamino-9-(6-chloro-3-pyridylmethyl)-8-hydroxyadenine

The title compound was obtained in the same manner as in Example 11using the compound obtained in Reference Example 5.

¹H NMR (DMSO-d₆) δ 10.10 (1H, brs), 8.56 (1H, d, J=1.9 Hz), 8.49–8.47(1H, m), 7.71–7.67 (1H, m), 7.38–7.33 (1H, m), 6.50 (2H, brs), 4.90 (2H,s), 4.14 (2H, t, J=6.6 Hz), 1.67–1.57 (2H, m), 1.41–1.30 (2H, m), 0.90(3H, t, J=7.3 Hz).

EXAMPLE 18 2-Butylamino-9-(2-chloro-3-pyridylmethyl)-8-hydroxyadenine

The title compound was obtained in the same manner as in Example 11using the compound obtained in Reference Example 5.

¹H NMR (DMSO-d₆) δ 9.76 (1H, brs), 8.35–8.32 (1H, m), 7.47–7.36 (2H, m),6.23 (1H, brt, J=5.7 Hz), 6.07 (2H, s), 4.88 (2H, s), 3.13–3.05 (2H, m),1.43–1.27 (2H, m), 1.24–1.16 (2H, m), 0.82 (3H, t, J=7.3 Hz).

EXAMPLE 19 2-Butylamino-8-hydroxy-9-(6-methoxy-3-pyridylmethyl)adenine

The title compound was obtained in the same manner as in Example 11using the compound obtained in Reference Example 5.

¹H NMR (DMSO-d₆) δ 10.07 (1H, brs), 8.17 (1H, d, J=2.4 Hz), 7.67 (1H,dd, J=2.4, 8.4 Hz), 6.82–6.76 (2H, m), 6.60 (2H, brs), 4.78 (2H, s),3.81 (3H, s), 3.25–3.17 (2H, m), 1.54–1.43 (2H, m), 1.38–1.25 (2H, m),0.89 (3H, t, J=7.3 Hz).

EXAMPLE 20 2-Butylamino-8-hydroxy-9-(2-pyridylmethyl)adenine

The title compound was obtained in the same manner as in Example 11using the compound obtained in Reference Example 5.

¹H NMR (DMSO-d₆) δ 10.88 (1H, s), 8.56–8.54 (1H, m), 8.05–7.89 (3H, m),7.46–7.41 (2H, m), 5.05 (3H, s), 3.19–3.14 (2H, m), 1.44–1.21 (4H, m),0.81 (3H, t, J=7.3 Hz).

EXAMPLE 21 2-Butylamino-8-hydroxy-9-(3-pyridylmethyl)adenine

The title compound was obtained in the same manner as in Example 11using the compound obtained in Reference Example 5.

¹H NMR (DMSO-d₆) δ 9.78 (1H, brs), 8.55 (1H, d, J=2.4 Hz), 8.47 (1H, dd,J=1.9, 4.9 Hz), 7.68 (1H, d, J=7.8 Hz), 7.34 (1H, dd, J=4.9, 7.8 Hz),6.21 (1H, brt, J=5.5 Hz), 6.05 (2H, brs), 4.84 (2H, s), 3.20–3.12 (2H,m), 1.47–1.39 (2H, m), 1.32–1.24 (2H, m), 0.87 (3H, t, J=7.3 Hz).

EXAMPLE 22 2-Butylamino-8-hydroxy-9-(4-pyridylmethyl)adenine

The title compound was obtained in the same manner as in Example 11using the compound obtained in Reference Example 5.

¹H NMR (DMSO-d₆) δ 11.05 (1H, brs), 8.76 (2H, d, J=8.7 Hz), 8.09–7.88(3H, m), 7.73 (2H, d, J=8.7 Hz), 5.09 (2H, s), 3.22–3.17 (2H, m),1.47–1.32 (2H, m), 1.29–1.18 (2H, m), 0.82 (3H, t, J=7.4 Hz).

EXAMPLE 232-Butylamino-9-(2,6-dichloro-3-pyridylmethyl)-8-hydroxyadenine

The title compound was obtained in the same manner as in Example 11using the compound obtained in Reference Example 5.

¹H NMR (DMSO-d₆) δ 9.82 (1H, brs), 7.61–7.51 (2H, m), 6.23 (1H, brt,J=5.4 Hz), 6.08 (2H, s), 4.87 (2H, s), 3.12–3.05 (2H, m), 1.40–1.19 (4H,m), 0.82 (3H, t, J=7.3 Hz).

EXAMPLE 242-Butylamino-9-(6-dimethylamino-3-pyridylmethyl)-8-hydroxyadenine

The title compound was obtained in the same manner as in Example 13using the compound obtained in Example 17 and an aqueous solution of 40%dimethylamine.

¹H NMR (DMSO-d₆) δ 9.61 (1H, brs), 8.10 (1H, d, J=2.2 Hz), 7.49 (1H, dd,J=2.2, 8.6 Hz), 6.56 (1H, d, J=8.6 Hz), 6.18 (1H, brt, J=5.7 Hz), 5.97(2H, brs), 4.65 (2H, s), 3.22–3.15 (2H, m), 2.97 (6H, s), 1.53–1.42 (2H,m), 1.38–1.24 (2H, m), 0.89 (3H, t, J=7.3 Hz).

EXAMPLE 25 2-Butoxy-8-hydroxy-9-(6-methyl-3-pyridylmethyl)adenine

The title compound was obtained in the same manner as in Example 1 usinga corresponding starting material.

¹H NMR (DMSO-d₆) δ 9.95 (1H, s), 8.42 (1H, d, J=2.2 Hz), 7.58 (1H, dd,J=2.2, 8.1 Hz), 7.20 (1H, d, J=8.1 Hz), 6.46 (2H, brs), 4.84 (2H, s),4.14 (2H, t, J=6.6 Hz), 2.41 (3H, s), 1.62 (2H, m), 1.37 (2H, m), 0.90(3H, t, J=7.3 Hz).

EXAMPLE 26 2-Butoxy-8-hydroxy-9-(2-methyl-3-pyridylmethyl)adenine

The title compound was obtained in the same manner as in Example 1 usinga corresponding starting material.

¹H NMR (DMSO-d₆) δ 10.01 (1H, brs), 8.33 (1H, d, J=3.1 Hz), 7.39 (1H, d,J=6.4 Hz), 7.15 (1H, dd, J=3.1, 6.4 Hz), 6.49 (2H, brs), 4.88 (2H, s),4.10 (2H, t, J=6.6 Hz), 2.59 (3H, s), 1.59 (2H, m), 1.34 (2H, m), 0.88(3H, t, J=7.3 Hz).

EXAMPLE 27 2-Butylamino-8-hydroxy-9-(6-methyl-3-pyridylmethyl)adenine

The title compound was obtained in the same manner as in Example 11using the compound obtained in Reference Example 5.

¹H NMR (DMSO-d₆) δ 9.78 (1H, s), 8.42 (1H, d, J=2.2 Hz), 7.57 (1H, dd,J=2.2, 8.0 Hz), 7.19 (1H, d, J=8.0 Hz), 6.22 (1H, t, J=7.1 Hz), 6.09(2H, brs), 4.78 (2H, s), 3.16 (2H, m), 2.41 (3H, s), 1.44 (2H, m), 1.28(2H, m), 0.87 (3H, t, J=9.6 Hz).

EXAMPLE 28 2-Butylamino-8-hydroxy-9-(2-methyl-3-pyridylmethyl)adenine

The title compound was obtained in the same manner as in Example 11using the compound obtained in Reference Example 5.

¹H NMR (DMSO-d₆) δ 9.70 (1H, s), 8.32 (1H, d, J=3.1 Hz), 7.37 (1H, d,J=7.7 Hz), 7.14 (1H, dd, J=3.1, 7.7 Hz), 6.20 (1H, t, J=6.4 Hz), 6.0(2H, brs), 4.82 (2H, s), 3.12 (2H, m), 2.60 (3H, s), 1.39 (2H, m), 1.25(2H, m), 0.84 (3H, t, J=7.1 Hz).

EXAMPLE 292-Butylamino-9-(2-chloro-6-methyl-3-pyridylmethyl)-8-hydroxyadenine

The title compound was obtained in the same manner as in Example 11using the compound obtained in Reference Example 5.

¹H NMR (DMSO-d₆) δ 9.74 (1H, brs), 7.33 (1H, d, J=5.8 Hz), 7.22 (1H, d,J=5.8 Hz), 6.24 (1H, m), 6.06 (2H, brs), 4.83 (2H, s), 3.09 (2H, m),2.42 (3H, s), 1.37 (2H, m), 1.25 (2H, m), 0.82 (3H, t, J=5.5 Hz).

EXAMPLE 30 2-Butylamino-8-hydroxy-9-(6-hydroxy-3-pyridylmethyl)adenine

The title compound was obtained in the same manner as in Example 11using the compound obtained in Reference Example 5.

¹H NMR (DMSO-d₆) δ 11.50 (1H, brs), 9.61 (1H, brs), 7.45 (1H, dd, J=2.6,9.5 Hz), 7.28 (1H, d, J=2.6 Hz), 6.28 (1H, d, J=9.5 Hz), 6.22 (1H, t,J=6.2 Hz), 6.00 (2H, brs), 4.53 (2H, s), 3.17 (2H, q, J=6.2 Hz), 1.45(2H, m), 1.30 (2H, m), 0.88 (3H, t, J=7.3 Hz).

EXAMPLE 31 8-Hydroxy-2-(2-methoxy)ethoxy-9-(3-pyridylmethyl)adenine

The title compound was obtained in the same manner as in Example 1 usinga corresponding starting material.

¹H NMR (DMSO-d₆) δ 10.02 (1H, brs), 8.57 (1H, s), 8.48 (1H, d, J=4.8Hz), 7.70 (1H, d, J=6.1 Hz), 7.36 (1H, dd, J=4.8, 6.1 Hz), 6.50 (2H,brs), 4.90 (2H, s), 4.27 (2H, t, J=4.6 Hz), 3.59 (2H, t, J=4.6 Hz), 3.27(3H, s).

EXAMPLE 32 8-Hydroxy-2-methoxy-9-(3-pyridylmethyl)adenine

The title compound was obtained in the same manner as in Example 1.

¹H NMR (DMSO-d₆) δ 10.04 (1H, brs), 8.57 (1H, s), 8.48 (1H, d, J=4.8Hz), 7.71 (1H, d, J=6.1 Hz), 7.35 (1H, dd, J=4.8, 6.1 Hz), 6.53 (2H,brs), 4.90 (2H, s), 3.76 (3H, s).

EXAMPLE 332-Butylamino-8-ethoxycarbonyloxy-9-(6-methoxy-3-pyridylmethyl)adenine

Triethylamine (100 μL, 0.75 mmol), ethyl chloroformate (67 μL, 0.70mmol), and dimethylaminopyridine (20 mg, 0.17 mmol) were added to asolution (15 ml) of the compound (200 mg, 0.58 mmol) obtained in Example19 in methylene chloride in that order, and the resultant was allowed toreact at room temperature for 15 hours. Water was added to the reactionsolution to extract an organic layer. The organic layer was washed withan aqueous solution of 5% citric acid and 10% saline solution and driedover anhydrous sodium sulfate. The solvent was then removed bydistillation. Hexane was added to the residue, and the solid wasprecipitated, followed by collection by filtration. Thus, 170 mg of thetitle compound was obtained as a white powdery solid (yield: 71%).

¹H NMR (CDCl₃) δ 8.33 (1H, d, J=1.9 Hz), 7.75 (1H, dd, J=1.9, 8.4 Hz),6.15 (2H, brs), 6.67 (1H, d, J=8.4 Hz), 4.87 (2H, s), 4.71 (1H, brt,J=5.4 Hz), 4.46 (2H, q, J=7.1 Hz), 3.90 (3H, s), 3.41–3.34 (2H, m),1.60–1.35 (7H, m), 0.96 (3H, t, J=7.3 Hz).

EXAMPLE 342-Butylamino-9-(6-chloro-3-pyridylmethyl)-8-ethoxycarbonyloxyadenine

The title compound was obtained in the same manner as in Example 33using the compound obtained in Example 17 and ethyl chloroformate.

¹H NMR (CDCl₃) δ 8.55 (1H, d, J=2.4 Hz), 7.81 (1H, dd, J=2.4, 8.4 Hz),7.27 (1H, d, J=8.4 Hz), 6.06 (2H, brs), 4.93 (2H, s), 4.83 (1H, brt,J=5.5 Hz), 4.47 (2H, q, J=7.1 Hz), 3.40–3.32 (2H, m), 1.59–1.36 (7H, m),0.95 (3H, t, J=7.3 Hz).

EXAMPLE 352-Butylamino-8-isopropoxycarbonyloxy-9-(6-methoxy-3-pyridylmethyl)adenine

The title compound was obtained in the same manner as in Example 33using the compound obtained in Example 19 and isopropyl chloroformate.

¹H NMR (CDCl₃) δ 8.32 (1H, d, J=2.2 Hz), 7.74 (1H, dd, J=2.2, 8.9 Hz),6.68 (1H, d, J=8.9 Hz), 6.08 (2H, brs), 5.23–5.13 (1H, m), 4.89 (1H,brt, J=5.8 Hz), 4.87 (2H, s), 3.91 (3H, s), 3.42–3.35 (2H, m), 1.60–1.52(2H, m), 1.48–1.37 (8H, m), 0.96 (3H, t, J=7.3 Hz).

EXAMPLE 362-Butylamino-9-(6-chloro-3-pyridylmethyl)-8-isopropoxycarbonyloxyadenine.

The title compound was obtained in the same manner as in Example 33using the compound obtained in Example 17 and isopropyl chloroformate.

¹H NMR (CDCl₃) δ 8.55 (1H, d, J=1.9 Hz), 7.80 (1H, dd, J=1.9, 8.4 Hz),7.27 (1H, d, J=8.4 Hz), 6.14 (2H, brs), 5.24–5.14 (1H, m), 4.96–4.92(3H, m), 3.40–3.33 (2H, m), 1.62–1.51 (2H, m), 1.45–1.34 (8H, m), 0.95(3H, t, J=7.3 Hz).

EXAMPLE 372-Butoxy-8-ethoxycarbonyloxy-9-(6-methoxy-3-pyridylmethyl)adenine

The title compound was obtained in the same manner as in Example 33using the compound obtained in Example 2 and ethyl chloroformate.

¹H NMR (CDCl₃) δ 8.33 (1H, d, J=2.4 Hz), 7.75 (1H, dd, J=2.4, 8.1 Hz),6.68 (1H, d, J=8.1 Hz), 6.15 (2H, brs), 4.93 (2H, s), 4.48 (2H, q, J=7.1Hz), 4.30 (2H, t, J=6.6 Hz), 3.90 (3H, s), 1.83–1.72 (2H, m), 1.53–1.43(5H, m), 0.98 (3H, t, J=7.3 Hz).

EXAMPLE 382-Butoxy-9-(6-chloro-3-pyridylmethyl)-8-ethoxycarbonyloxyadenine

The title compound was obtained in the same manner as in Example 33using the compound obtained in Example 1 and ethyl chloroformate.

¹H NMR (CDCl₃) δ 8.56 (1H, d, J=2.4 Hz), 7.81 (1H, dd, J=2.4, 8.4 Hz),7.29 (1H, d, J=8.4 Hz), 7.28 (2H, brs), 4.99 (2H, s), 4.49 (2H, q, J=7.0Hz), 4.28 (2H, t, J=6.6 Hz), 1.81–1.71 (2H, m), 1.52–1.43 (5H, m), 0.97(3H, t, J=7.3 Hz).

EXAMPLE 392-Butoxy-9-(2-chloro-3-pyridylmethyl)-8-ethoxycarbonyloxyadenine

The title compound was obtained in the same manner as in Example 33using the compound obtained in Example 5 and ethyl chloroformate.

¹H NMR (DMSO-d₆) δ 8.37–8.35 (1H, m), 7.73–7.69 (1H, m), 7.41–7.37 (1H,m), 7.09 (2H, brs), 4.95 (2H, s), 4.39 (2H, q, J=7.2 Hz), 4.12 (2H, t,J=6.6 Hz), 1.61–1.53 (2H, m), 1.37–1.29 (5H, m), 0.87 (3H, t, J=7.3 Hz).

EXAMPLE 40 2-Butoxy-8-methoxycarbonyloxy-9-(3-pyridylmethyl)adenine

The title compound was obtained in the same manner as in Example 33using the compound obtained in Example 8 and methyl chloroformate.

¹H NMR (CDCl₃) δ 8.77 (1H, d, J=2.2 Hz), 8.56–8.53 (1H, m), 7.85–7.81(1H, m), 7.25 (2H, brs), 7.24–7.22 (1H, m), 5.02 (2H, s), 4.30 (2H, t,J=6.6 Hz), 4.05 (3H, s), 1.82–1.72 (2H, m), 1.53–1.42 (2H, m), 0.97 (3H,t, J=7.3 Hz).

EXAMPLE 412-Butoxy-8-(n-pentyloxy)carbonyloxy-9-(3-pyridylmethyl)adenine

The title compound was obtained in the same manner as in Example 33using the compound obtained in Example 8 and n-pentyl chloroformate.

¹H NMR (DMSO-d₆) δ 8.59 (1H, d, J=1.9 Hz), 8.51–8.48 (1H, m), 7.75–7.72(1H, m), 7.39–7.34 (1H, m), 7.07 (2H, brs), 4.92 (2H, s), 4.32 (2H, t,J=6.6 Hz), 4.18 (2H, t, J=6.5 Hz), 1.71–1.61 (4H, m), 1.41–1.31 (6H, m),0.93–0.85 (6H, m).

EXAMPLE 422-Butoxy-8-(cyclohexyloxy)carbonyloxy-9-(3-pyridylmethyl)adenine

The title compound was obtained in the same manner as in Example 33using the compound obtained in Example 8 and cyclohexyl chloroformate.

¹H NMR (DMSO-d₆) δ 8.60 (1H, d, J=1.9 Hz), 8.51–8.49 (1H, m), 7.76–7.72(1H, m), 7.39–7.35 (1H, m), 7.07 (2H, brs), 4.96–4.93 (3H, m), 4.18 (2H,t, J=6.5 Hz), 1.86–1.58 (8H, m), 1.44–1.33 (6H, m), 0.91 (3H, t, J=7.4Hz).

EXAMPLE 43 8-(Allyloxy)carbonyloxy-2-butoxy-9-(3-pyridylmethyl)adenine

The title compound was obtained in the same manner as in Example 33using the compound obtained in Example 8 and allyl chloroformate.

¹H NMR (DMSO-d₆) δ 8.61 (1H, d, J=1.9 Hz), 8.51–8.49 (1H, m), 7.77–7.74(1H, m), 7.39–7.35 (1H, m), 7.25 (1H, dd, J=6.5, 13.8 Hz), 7.03 (2H,brs), 5.06 (1H, dd, J=1.9, 13.8 Hz), 4.93 (2H, s), 4.86 (1H, dd, J=1.9,6.5 Hz), 4.19 (2H, t, J=6.6 Hz), 1.64–1.41 (2H, m), 1.39–1.33 (2H, m),0.91 (3H, t, J=7.4 Hz).

EXAMPLE 44 8-Acetyloxy-2-butoxy-9-(6-chloro-3-pyridylmethyl)adenine

The title compound was obtained in the same manner as in Example 33using the compound obtained in Example 17 and acetic anhydride.

¹H NMR (CDCl₃) δ 8.56 (1H, d, J=2.4 Hz), 7.80 (1H, dd, J=2.4, 8.4 Hz),7.30 (1H, d, J=8.4 Hz), 7.28 (2H, brs), 5.00 (2H, s), 4.29 (2H, t, J=6.5Hz), 2.72 (3H, s), 1.82–1.71 (2H, m), 1.52–1.42 (2H, m), 0.97 (3H, t,J=7.3 Hz).

EXAMPLE 45 8-Propionyloxy-2-butoxy-9-(6-chloro-3-pyridylmethyl)adenine

The title compound was obtained in the same manner as in Example 33using the compound obtained in Example 17 and propionyl chloride.

¹H NMR (CDCl₃) δ 8.55 (1H, d, J=2.4 Hz), 7.80 (1H, dd, J=2.4, 8.1 Hz),7.30 (1H, d, J=8.1 Hz), 7.28 (2H, brs), 5.00 (2H, s), 4.29 (2H, t, J=6.5Hz), 3.14 (2H, q, J=7.4 Hz), 1.82–1.71 (2H, m), 1.55–1.42 (2H, m), 1.23(3H, t, J=7.3 Hz), 0.97 (3H, t, J=7.3 Hz).

EXAMPLE 46 8-Benzoyloxy-2-butoxy-9-(6-methyl-3-pyridylmethyl)adenine

The title compound was obtained in the same manner as in Example 33using the compound obtained in Example 25 and benzoyl chloride.

¹H NMR (CDCl₃) δ 8.64 (1H, d, J=2.4 Hz), 7.77 (2H, d, J=7.3 Hz), 7.69(1H, dd, J=2.4, 8.1 Hz), 7.63 (1H, t, J=7.3 Hz), 7.49 (2H, t, J=7.3 Hz),7.09 (1H, d, J=8.1 Hz), 5.76 (2H, brs), 4.95 (2H, s), 4.34 (2H, t, J=6.6Hz), 2.52 (3H, s), 1.78 (2H, m), 1.52 (2H, m), 0.99 (3H, t, J=7.3 Hz).

EXAMPLE 47 8-Benzoyloxy-2-butylamino-9-(6-methyl-3-pyridylmethyl)adenine

The title compound was obtained in the same manner as in Example 33using the compound obtained in Example 27 and benzoyl chloride.

¹H NMR (CDCl₃) δ 8.63 (1H, d, J=2.0 Hz), 7.74 (2H, d, J=7.4 Hz), 7.69(1H, dd, J=2.0, 7.9 Hz), 7.61 (1H, t, J=7.4 Hz), 7.47 (2H, t, J=7.4 Hz),7.08 (1H, d, J=7.9 Hz), 5.57 (2H, brs), 4.88 (2H, s), 4.84 (1H, t, J=5.9Hz), 3.40 (2H, m), 2.52 (3H, s), 1.58 (2H, m), 1.42 (2H, m), 0.97 (3H,t, J=7.3 Hz).

EXAMPLE 482-Butoxy-8-(4-methyl)benzoyloxy-9-(6-methyl-3-pyridylmethyl)adenine

The title compound was obtained in the same manner as in Example 33using the compound obtained in Example 25 and p-toluoyl chloride.

¹H NMR (DMSO-d₆) δ 8.44 (1H, s), 7.73 (2H, d, J=8.2 Hz), 7.62 (1H, d,J=8.0 Hz), 7.30 (2H, d, J=8.2 Hz), 7.20 (1H, d, J=8.0 Hz), 6.84 (2H,brs), 4.84 (2H, s), 4.22 (2H, t, J=6.6 Hz), 2.42 (3H, s), 2.40(3H, s),1.66 (2H, m), 1.41 (2H, m), 0.92 (3H, t, J=7.4 Hz).

EXAMPLE 492-Butylamino-8-(4-methyl)benzoyloxy-9-(6-methyl-3-pyridylmethyl)adenine

The title compound was obtained in the same manner as in Example 33using the compound obtained in Example 27 and p-toluoyl chloride.

¹H NMR (DMSO-d₆) δ 8.43 (1H, s), 7.69 (2H, d, J=8.2 Hz), 7.62 (1H, d,J=8.0 Hz), 7.28 (2H, d, J=8.2 Hz), 7.19 (1H, d, J=8.0 Hz), 6.71 (1H,brs), 6.25 (2H, brs), 4.80 (2H, s), 3.22 (2H, t, J=6.6 Hz), 2.42 (3H,s), 2.39(3H, s), 1.46 (2H, m), 1.30 (2H, m), 0.89 (3H, t, J=7.4 Hz).

EXAMPLE 50 2-Butylamino-8-hydroxy-9-(1-naphthylmethyl)adenine

The title compound was obtained in the same manner as in Example 11using the compound obtained in Reference Example 5.

¹H NMR (DMSO-d₆) δ 9.79 (1H, s), 8.39–8.41 (1H, m), 7.94–7.97 (1H, m),7.83–7.86 (1H, m), 7.55–7.59 (2H, m), 7.40–7.46 (1H, m), 7.26 (1H, m),6.17 (1H, t, J=5.8 Hz), 6.05 (2H, s), 5.28 (2H, s), 3.09–3.16 (2H, m),1.36–1.44 (2H, m), 1.21–1.29 (2H, m), 0.83 (3H, t, J=7.4 Hz).

EXAMPLE 51 2-Butylamino-8-hydroxy-9-(2-naphthylmethyl)adenine

The title compound was obtained in the same manner as in Example 11using the compound obtained in Reference Example 5.

¹H NMR (DMSO-d₆) δ 9.69 (1H, s), 7.84–7.89 (3H, m), 7.74 (1H, s),7.47–7.25 (3H, m), 6.21 (1H, t, J=5.8 Hz), 6.03 (2H, s), 4.97 (2H, s),3.12–3.20 (2H, m), 1.41–1.46 (2H, m), 1.22–1.31 (2H, m), 0.83 (3H, t,J=7.4 Hz)

EXAMPLE 52 2-Butoxy-8-hydroxy-9-(1-naphthylmethyl)adenine

The title compound was obtained in the same manner as in Example 1 usinga corresponding starting material.

¹H NMR (DMSO-d₆) δ 10.21 (1H, s), 8.37–8.41 (1H, m), 7.85–7.98 (2H, m),7.55–7.60 (2H, m), 7.41–7.47 (1H, m), 7.25–7.28 (1H, m), 6.52 (2H, s),5.34 (2H, s), 4.10 (2H, d, J=6.6 Hz), 1.55–1.61 (2H, m), 1.29–1.38 (2H,m), 0.87 (3H, t, J=7.3 Hz).

EXAMPLE 53 2-Butoxy-8-hydroxy-9-(2-naphthylmethyl)adenine

The title compound was obtained in the same manner as in Example 1 usinga corresponding starting material.

¹H NMR (DMSO-d₆) δ 10.12 (1H, s), 7.87–7.90 (3H, m), 7.76 (1H, s),7.46–7.51 (3H, m), 6.45 (2H, s), 5.02 (2H, s), 4.14 (2H, d, J=6.6 Hz),1.55–1.63 (2H, m), 1.31–1.39 (2H, m), 0.88 (3H, t, J=7.3 Hz).

EXAMPLE 54 2-Butylamino-8-hydroxy-9-(5-chloro-2-thienylmethyl)adenine

The title compound was obtained in the same manner as in Example 11using the compound obtained in Reference Example 5.

¹H NMR (DMSO-d₆) δ 9.85 (1H, s), 6.96 (1H, d, J=3.8 Hz), 6.91 (1H, d,J=3.8 Hz), 6.23 (1H, t, J=5.4 Hz), 6.07 (2H, s), 4.87 (2H, s), 3.15–3.23(2H, m), 1.43–1.53 (2H, m), 1.24–1.37 (2H, m), 0.89 (3H, t, J=7.3 Hz).

EXAMPLE 55 2-Butylamino-8-hydroxy-9-(6-methyl-3-pyridylmethyl)adeninemonosulfate

0.5N sulfuric acid (30.8 ml) was added to a methanol solution (520 ml)of the compound of Example 27 (2.52 g, 7.70 mmol), and the precipitatedcrystal was collected by filtration. Thus, the title compound wasobtained.

mp: 249–252° C.

Calc.: C, 45.17; H, 5.45; N, 23.04; S, 7.54.

Anal.: C, 44.96; H, 5.56; N, 22.90; S, 7.53.

EXAMPLE 56 Interferon-inducing Activity in Mouse Spleen Cell (in vitro)

Spleen was extirpated from a C3H/HeJ mouse strain (male, 8 to 10 weeksold), and 2×10⁶ cells/ml of a splenic cell suspension was prepared usingMEM medium containing 5% FBS. The resulting suspension was fractionatedto each well of a 24-well microplate in amounts of 0.5 ml each.Thereafter, a test compound (comprising 0.2% DMSO) that was diluted inthe same medium was added to each well in amounts of 0.5 ml each, andculture was conducted in an incubator in the presence of 5% CO₂ at 37°C. for 24 hours. The culture solution was aseptically filtered through a0.2-μm filter to obtain a culture supernatant. The interferon titer inthe culture supernatant was quantified by the bioassay described in J.A. Armstrong, Methods in Enzymology 78, 381-7. More specifically, 1×10⁴cells/50 μl of mouse fibroblasts, L929, were cultured in a 96-wellculture plate for 24 hours, and 50 μl of diluted culture supernatant wasadded thereto, followed by culturing for an additional 24 hours.Subsequently, 100 μl each of vesicular stomatitis virus was added, andthe cytopathogenic effect 44 hours after the virus infection wasconfirmed by crystal violet staining. Quantification was carried out bydissolving the dye with the aid of an aqueous solution of 2% sodiumdeoxycholate and assaying the absorbance at 595 nm.9-Benzyl-2-butylamino-8-hydroxyadenine (a compound described in Example24 of WO 99-28321) as Reference Compound 1,9-benzyl-2-butoxy-8-hydroxyadenine (a compound described in Example 19of WO 99-28321) as Reference Compound 2, R-837 (Imiquimod) asComparative Example 1, andR-848(1-(2-hydroxy-2-methylpropyl)-2-methoxyethyl-1H-imidazo[4,5-c]quinoline-4-amine)as Comparative Example 2 were used. Table 2 shows the minimum effectiveconcentration of each compound.

TABLE 2 Interferon-inducing activity Minimum effective Compoundconcentration (nM) Example 1 1 Example 2 1 Example 3 1 Example 4 10Example 5 3 Example 6 1 Example 7 1 Example 8 1 Example 9 3 Example 1010 Example 11 3 Example 12 10 Example 13 3 Example 14 1 Example 15 1Example 16 1 Example 17 3 Example 18 10 Example 19 3 Example 20 30Example 21 3 Example 22 10 Example 23 10 Example 24 3 Example 25 1Example 26 1 Example 27 3 Example 28 10 Example 29 10 Reference Compound1 100 Reference Compound 2 1 Comparative Example 1 300 ComparativeExample 2 3

EXAMPLE 57 Interferon-inducing Activity in Mouse (in vivo)

A test compound was suspended in an aqueous solution of 0.5%carboxymethylcellulose, and the resulting suspension was orallyadministered to a Balb/c male mouse. Two hours later, blood was sampledfrom its heart, and the interferon titer in blood serum was assayed inthe same manner as in Example 56. Table 3 shows the results.

TABLE 3 Interferon-inducing activity (U/ml) Dosage (mg/kg) 0.01 0.03 0.10.3 Example 1 123 ± 87  322 ± 95  623 ± 32  Example 2 25 ± 17 388 ± 87 1211 ± 263  2559 ± 495  Example 3 353 ± 73  1966 ± 532  Example 5 133 ±33  473 ± 9  Example 6 569 ± 42  1222 ± 248  Example 7 347 ± 149 845 ±22  Example 8 13 ± 5  167 ± 97  725 ± 141 936 ± 438 Example 9 539 ± 107Example 10 89 ± 22 409 ± 267 733 ± 256 Example 11 279 ± 177 568 ± 160Example 12 31 ± 5  Example 13 304 ± 138 Example 14 570 ± 63  Example 1552 ± 32 603 ± 147 Example 16 251 ± 46  716 ± 155 Example 17 31 ± 23 183± 43  999 ± 379 Example 18 94 ± 49 Example 19 14 ± 5  199 ± 84  383 ±122 601 ± 187 Example 21 15 ± 8  290 ± 134 571 ± 164 Example 22 21 ± 9 332 ± 83  Example 23 42 ± 7  414 ± 118 Example 24 403 ± 146 Example 2565 ± 52 151 ± 29  753 ± 140 721 ± 299 Example 26 121 ± 11  433 ± 366 780± 190 Example 27 14 ± 3  324 ± 66  804 ± 274 Example 28 186 ± 62  1462 ±260  Example 29 619 ± 268 Reference Compound 55 ± 25 275 ± 165 1Reference Compound 60 ± 40 186 ± 42  317 ± 160 2 Comparative Example1638 ± 246  1961 ± 950  2

EXAMPLE 58 Interferon-inducing Activity in Cynomolgus Monkey (in vivo)

A test compound was suspended in an aqueous solution of 0.5%carboxymethylcellulose, and 10 mg/kg of the resulting suspension wasorally administered to a group of five male cynomolgus monkeys. Bloodwas sampled with the elapse of time, and the interferon titer in bloodserum was assayed in the same manner as in Example 56. The interferontiters in blood serum four hours after the administration (average±SE)were 13,876±825 U/ml in the compound of Example 17, 12,173±6619 U/ml inthe compound of Example 19, 14,488±6365 U/ml in the compound of Example27, and 18,305±5578 U/ml in the compound of Reference Example 2. Theseresults indicate that interferon-inducing activity of each case wassubstantially the same. While vomition was observed in 4 out of 5samples in the compound of Reference Example 2, no vomition was observedin any sample in the case of the compound according to the presentinvention.

EXAMPLE 59 Interferon-inducing Activity in Human Peripheral BloodMononuclear Cells (PBMC)

Peripheral bloods were sampled from 5 healthy volunteers using a syringecontaining heparin, and peripheral blood mononuclear cells (PBMC) wereprepared by density gradient centrifugation utilizing the Lymphoprep™(NYCOMED PHARMA AS). PBMCs were washed twice in serum-free RPMI 1640medium and adjusted at 1×10⁶ cells/ml in RPMI 1640 medium comprising 10%fetal bovine serum. The product was cultured in the presence of a testcompound dissolved in dimethyl sulfoxide (final concentration: 0.1%) inan incubator in the presence of 5% CO² at 37° C. for 24 hours. As acontrol, 0.1% dimethyl sulfoxide containing no test compound was used.The culture supernatant was aseptically collected by filtration.Thereafter, the supernatant was cryopreserved at −20° C. or lower untilit was subjected to the assay for IFN-inducing activity. Human IFN-α inthe culture supernatant was quantified using a highly sensitive ELISAsystem (Amersham). Table 4 shows the results, wherein (−) indicates adetection limit (1.25 pg/ml) or lower and NT refers to “not tested.”

TABLE 4 Interferon-inducing activity (pg/ml) Concentration (nM) 0.3 1 310 30 Example 17 NT 5 ± 3 17 ± 17 50 ± 33 61 ± 38 Example 19 NT 5 ± 1 12± 11 48 ± 34 60 ± 33 Example 25 7 ± 3 28 ± 24 46 ± 34 NT NT Example 27NT 6 ± 3 26 ± 22 56 ± 37 59 ± 33 Comparative Example 2 — — 6 ± 5 NT NTReference Compound 2 NT — 7 23 ± 22 64 ± 40

EXAMPLE 60 Inhibitory Activity Against Th2 Cytokine Produced fromSensitized Spleen Cells

A 7-week-old BALB/c mouse was immunized intraperitoneally with aluminumhydroxide gel (4 mg, 100 μl) having 10 μg of ovalbumin adsorbed thereon,and it was subjected to additional immunization with the same agent 14days later. Seven days thereafter, spleen was taken out, and suspendedin RPMI-1640 comprising inactivated fetal bovine serum (10%),2-mercaptoethanol (50 μl), penicillin G (100 U/ml), and streptomycin(100 μg/ml). Thus, a splenic cell suspension was prepared. Ovalbumin(0.5 mg/ml) and a test compound were added to a splenic cell suspension(5×10⁶ cell/200 μl/well), and the resultant was cultured at 37° C. inthe presence of 5% CO₂ for 3 days. The cytokine level in the culturesupernatant was quantified by ELISA. IFN-γ and IL-4 were assayed using akit available from Amersham, and IL-5 was assayed using a kit availablefrom Endogen. Table 5 shows the results.

TABLE 5 Concentration (nM) 0.1 1 10 100 Inhibitory activity against IL-4production (% of control) Example 1 98 7 2 <1 Example 2 96 4 <1 <1Example 10 — 54 3 <1 Example 17 — 40 <1 <1 Example 19 — 32 <1 <1 Example20 — 106 23 2 Example 21 — 53 1 <1 Example 22 — 88 9 1 Example 25 86 2<1 <1 Example 27 — 30 1 <1 Comparative Example 1 — 18 1 <1 ComparativeExample 2 90 24 1 <1 Reference Compound 1 — — 109 24 Reference Compound2 107 48 1 <1 Inhibitory activity against IL-5 production (% of control)Example 1 116 41 16 15 Example 2 98 37 14 12 Example 10 — 91 32 15Example 17 — 77 24 10 Example 19 — 83 16 13 Example 20 — 106 71 19Example 21 — 97 23 15 Example 22 — 115 50 18 Example 25 102 31 13 13Example 27 — 68 20 12 Comparative Example 1 — 54 15 10 ComparativeExample 2 106 73 18 10 Reference Compound 1 — — 92 69 Reference Compound2 99 79 16 11

EXAMPLE 61 Gastrointestinal Absorption in Rat

A test compound was suspended in an aqueous solution of 0.5%carboxymethylcellulose, and the resulting suspension was orallyadministered to an SD male rat. Blood was sampled with the elapse oftime, and the level of the drug in blood was assayed by HPLC. Thefollowing table shows the Cmax and Tmax values.

TABLE 6 Cmax and Tmax Dose (mg/kg) Cmax (ng/ml) Tmax (hr) Example 17 3310 1 Example 19 3 188 4 Hydrochloride of Example 3 18 1 25 10 150 0.25Example 27 3 565 0.5 Comparative Example 1 3 90 0.5 Comparative Example2 3 19 1 10 15 0.5

EXAMPLE 62 Solubility

5.53% citric acid (monohydrate) and 1.75% disodium phosphate (anhydrous)were mixed together to prepare buffers (pH 2.5, 5.5, 7.4). A compoundwas added thereto, the mixture was stirred in a vortex mixer andsubjected to ultrasonication for 30 minutes. Thereafter, the resultantwas stirred in a vortex mixer again and then centrifuged at 15,000 rpmfor 20 minutes. The levels of the compounds in the supernatants werethen quantified by HPLC. The following table shows these concentrationlevels.

TABLE 7 (μg/ml) pH 2.5 pH 5.5 pH 7.4 Example 8 784 20 18 Example 9 350 43 Example 10 34 15 10 Example 15 140 1 <1 Example 16 293 NT NT Example19 130 2 2 Example 20 8,813 NT NT Example 21 15,000 45 64 Example22 >80,000 73 16 Example 24 27,000 22 1 Example 25 >1,000 5 3 Example26 >1,000 6 3 Example 27 610 5 2 Example 28 >1,000 8 4 Example 31 >1,000353 322 Example 32 >1,000 82 25 Reference Compound 1 26 <1 <1 ReferenceCompound 2 2 <1 <1

EXAMPLE 63 Medicinal Effect of the Compound of Example 27 in a Rat Modelof Eosinophil Leukocytic Infiltration

A rat was immunized intraperitoneally with 1 ml of a solution containing1 mg of ovalbumin (OVA) and 100 mg of Al(OH)₃ on day 0 and day 7. On day14, a 1% OVA solution was sprayed for 15 minutes using a ultrasonicnebulizer to induce reactions. A test compound was administeredintratracheally 2.5 hours before the induction. Bronchoalveolar lavagewas performed 24 hours after the induction, and eosinocytes in the washwas stained with Hinkelman to count the number of stained cells.Sensi.−/Challe.+, CMC-Na, and Fluticasone were used as controls. FIG. 1and the following table show the results.

TABLE 8 ×10⁴ cells Compound Standard (intratracheal administration)Average deviation Standard error Sensi.−/Challe.+ 26.22 15.60 6.37CMC-Na 319.55 281.89 115.08 Example 27 (0.001 mg/kg) 383.85 392.01160.04 Example 27 (0.01 mg/kg) 186.77 161.86 66.08 Example 27 (0.1mg/kg) 46.84 51.84 21.16 Fluticasone (0.01 mg/kg) 300.07 231.84 94.65

EXAMPLE 64 Medicinal Effect of the Compound of Example 17 in a MouseModel of Active Cutaneous Anaphylaxis

A mouse was immunized intraperitoneally with 500 μl of a solutioncontaining 2 μg of ovalbumin (OVA) and 5 mg of Al(OH)₃ on day 0. On day14, 20 μl of 1 mg/ml OVA solution was intradermally injected in the leftauricle under ether anesthesia to induce the reaction. A test compoundwas applied to both surfaces of the left auricle in amounts of 10 μleach 2 hours before the induction. The thickness of the auricle wasmeasured using a micrometer 24 hours after the induction. Acetone wasused as a control. FIG. 2 and the following table show the results.

TABLE 9 Ear swelling (mm) Compound Average Standard deviation Standarderror Acetone 0.034 0.021 0.009 Example 17 (4 μg/ear) 0.046 0.024 0.010Example 17 (40 μg/ear) 0.048 0.013 0.005 Example 17 (400 μg/ear) 0.0140.008 0.003

EXAMPLE 65 Antitumor Effect of the Compound of Example 27 inTumor-bearing Mouse Model

Murine renal adenocarcinoma-derived Renca cells (obtained from IwateMedical University) were intradermally transplanted to the left ventralportions of 6-week-old BALB/c male mice (Charles River Japan, Inc.) at5×10⁴ cells/0.05 ml/mouse. Their body weights were measured on the nextday, and they were divided into 5 groups (each group comprising 6 mice)in such a manner that the average body weights were substantially thesame among groups. Vehicles (an aqueous solution of 0.5%carboxymethylcellulose (hereinafter referred to as “CMC-Na”)) and thecompound of Example 27 (1 mg/kg and 3 mg/kg) were forcibly administeredorally using an oral Sonde (10 ml/kg). Mouse interferon α (hereinafterreferred to as “mIFN-α”) was intradermally administered to mice throughtheir backs in amounts of 1×10⁴ U/0.1 ml and 5×10⁴ U/0.1 ml per mouse.Administration was carried out 5 times every 4 days. The longer diameter(L, mm) and the shorter diameter (W, mm) of the generated tumors weremeasured twice a week, and the tumor volumes (V, mm³) were calculated(V=L×W²). Also, significant difference was examined in accordance withSteel's multiple comparison. The SAS system for Windows Release 8.01(SAS Institute Inc., Cary, N.C., U.S.A.) was used for the examination.

A surveillance period of about 30 days after the transplantation wasprovided, the tumor volume and the body weight were monitored, and anantitumor effect against the Renca cells was evaluated. The averagetumor volume (n=6) of each agent was compared with those of casesinvolving vehicle administration. The results thereof are shown in FIG.3. As a result, the tumor volume in the groups to which the compound ofExample 27 and mIFN-α were administered was significantly smaller thanthat in the group to which vehicles had been administered (P<0.05).Administration of the compound of Example 27 was found to exhibit theantitumor effect equivalent to or higher than that attained by theadministration of mIFN-α.

EXAMPLE 66 Antitumor Effect of the Compound of Example 27 in a MouseModel of Spontaneous Metastasis (Inhibitory Effect Against Metastasis)

OV2944-HM-1 cells (obtained from Hiroshima University) derived frommouse ovarian cancer that is highly metastatic to the lymph nodes wereintradermally transplanted to the buttocks of 6-week-old B6C3F1 femalemice (Charles River Japan, Inc.) in amounts of 1×10⁶ cells/0.05ml/mouse. Ten days after the transplantation, the primary tumor wasexcised under Nembutal anaesthesia. Adhesives (Aron Alpha) were appliedto the excised portions, and the stumps were sewed up with wound clips.The next day, body weights were measured, and they were divided into 3groups (each group comprising 6 mice) in such a manner that the averagebody weights among groups were substantially the same. Vehicles (aqueoussolutions of 0.5% CMC-Na) and the compound of Example 27 (3 mg/kg) wereforcibly administered orally using an oral Sonde (10 ml/kg). Also, 5×10⁴U/0.1 ml/mouse of mIFN-α was intradermally administered through theirbacks. Administration was carried out 5 times every 4 days. Regionallymph nodes (mouse cervical, brachium, axillary cavity) were extirpated35 days after the transplantation, and their wet weights were measured.Simultaneously, lungs were extirpated to visually inspect themetastasis. Also, significant difference was examined in accordance withSteel's multiple comparison. The SAS system for Windows Release 8.01(SAS Institute Inc., Cary, N.C., U.S.A.) was used for the examination.

As shown in FIG. 4, the largest metastatic focus was the mouse cervicallymph node located close to the primary tumor, followed by the axillarycavity lymph node and brachium lymph node. The weight of each metastasislymph node of the group to which the compound of Example 27 wasadministered was smaller than those attained from the group to whichvehicles were administered. This indicates that the compound of Example27 exhibits a metastasis-inhibiting effect. The HM-1 cells exhibit notonly lymph node metastasis but also highly frequent pulmonarymetastasis. Thus, pulmonary metastasis was examined. As shown in thetable below, pulmonary metastasis was observed in 5 out of 6 mice in thegroup to which vehicles had been administered based on visualinspection; however, it was not observed at all with the administrationof the compound of Example 27. This indicates that the compound ofExample 27 can potently inhibit pulmonary metastasis in addition of itsability to inhibit lymph node metastasis. In contrast, mIFN-α did notinhibit lymph node metastasis, and the frequency of pulmonary metastasiswas the same as that attained in the group to which vehicles had beenadministered.

TABLE 10 The number of mice which exhibited pulmonary metastasis in 6mice Vehicle 5 Mouse interferon α 5 Compound of Example 27 0

EXAMPLE 67 Preparation Example

Tablets having the following composition were produced in accordancewith a conventional technique.

Compound of Example 25  10 mg Lactose 600 mg Starch 250 mgHydroxypropylcellulose  30 mg Calcium stearate  5 mg

EXAMPLE 68 Preparation Example

Solid dispersants having the following composition were produced inaccordance with a conventional technique.

Compound of Example 27  20 mg Nikkol (surfactant)  5 mgHydroxypropylcellulose 200 mg Methanol  2 ml Dichloromethane  2 ml

All publications cited herein are incorporated herein by reference intheir entirety.

INDUSTRIAL APPLICABILITY

The adenine derivative according to the present invention has selectiveand significant interferon-inducing activity. The adenine derivativeaccording to the present invention accelerates interferon secretion inliving organisms, and thus, is useful for prevention or treatment of,for example, viral diseases such as hepatitis B, hepatitis C, or AIDS orcancerous diseases for which interferon is effective. The adeninederivative according to the present invention is of low molecularweight. Accordingly, it can be orally administered, unlike interferonpreparations. In addition, the adenine derivative according to thepresent invention is a compound having excellent water solubility andhigh gastrointestinal absorption. Further, the adenine derivativeaccording to the present invention selectively inhibits the productionof inflammatory cytokines such as IL-4 or IL-5 that are discharged fromTh2 cells. Accordingly, it is useful as a preventive or therapeuticagent for diseases such as asthma or atopic dermatitis with which Th2cells are deeply involved.

1. An adenine derivative, a tautomer thereof, or a pharmaceuticallyacceptable salt thereof represented by formula (I):

wherein X represents NR³ (wherein R³ represents a hydrogen atom or C₁₋₃alkyl), an oxygen atom, or a sulfur atom; R¹ represents substituted orunsubstituted alkyl, substituted or unsubstituted alkenyl, substitutedor unsubstituted alkynyl, substituted or unsubstituted aryl, substitutedor unsubstituted heteroaryl, substituted or unsubstituted cycloalkyl, orsubstituted or unsubstituted cycloalkenyl; R² represents hydroxyl,mercapto, C¹⁻⁸ acyloxy, or C₂₋₈ alkoxycarbonyloxy; and Y represents asubstituted or unsubstituted naphthalene ring, a substituted orunsubstituted 5- or 6-membered monocyclic aromatic hetero ringcontaining 1 or 2 hetero atoms selected from the group consisting ofnitrogen, oxygen, and sulfur atoms, or a substituted or unsubstitutedfused bicyclic aromatic hetero ring containing 1 or 2 hetero atomsselected from the group consisting of nitrogen, oxygen, and sulfuratoms.
 2. The compound according to claim 1, wherein, in formula (I), R¹represents C₁₋₈ alkyl, C₂₋₈ alkenyl, C₂₋₈ alkynyl, C₂₋₈ alkoxyalkyl,C₁₋₈ hydroxyalkyl, aryl, heteroaryl, aralkyl, heteroarylalkyl,cycloalkyl or cycloalkenyl.
 3. The compound according to claim 1,wherein, in formula (I), R¹ represents C₁₋₆ alkyl, cycloalkyl, orcycloalkenyl.
 4. The compound according to claim 1, wherein, in formula(I), X represents NH.
 5. The compound according to claim 1, wherein, informula (I), X represents an oxygen atom.
 6. The compound according toclaim 1, wherein, in formula (I), Y represents a unsubstituted orsubstituted pyridine ring or a substituted or unsubstituted pyrazinering.
 7. The compound according to claim 1, wherein, in formula (I), Yrepresents a unsubstituted or substituted naphthalene ring or asubstituted or unsubstituted thiophene ring.
 8. The compound accordingto claim 1, wherein, in formula (I), Y has 1 to 4 substituents when Y isa pyridine ring, and 1 to 3 substituents when Y is a pyrazine ring atany positions, wherein the substituent is selected from the groupconsisting of C₁₋₄ alkyl, C₁₋₄ alkoxy, hydroxyl, mercapto, C₁₋₄alkylthio, a halogen atom, amino, C₂₋₈ dialkylamino, C₁₋₄monoalkylamino, pyrrolidinyl, piperidino, and morpholino.
 9. Thecompound according to claim 1, wherein, in formula (I), Y represents apyridine ring which may have a substituent selected from the groupconsisting of C₁₋₄ alkyl, C₁₋₄ alkoxy, hydroxyl, mercapto, C₁₋₄alkylthio, a halogen atom, amino, C₂₋₈ dialkylamino, C₁₋₄monoalkylamino, pyrrolidinyl, piperidino, and morpholino; R¹ representsC₁₋₆ alkyl; and R² represents hydroxyl.
 10. The compound according toclaim 9, wherein, in formula (I), X represents NH or an oxygen atom. 11.2-Butylamino-8-hydroxy-9-(6-methyl-3-pyridylmethyl)adenine or apharmaceutically acceptable salt thereof.
 12. A pharmaceuticalcomposition comprising the compound according to any one of claims 1 to10 or 11 as an active ingredient, and a carrier.